What the...?

My summer dating spree has been going full force. And naturally, that means more unexplained behavior and new experiences.

A couple of weeks ago I was very excited about the prospect of a new guy. His emails were witty and he was very good looking. There seemed to be some potential. We talked about grabbing drinks on a Monday night. Sunday evening he calls me for the first time...all prior communication had been done through email. I was out so he left me a voicemail. He was saying that a work thing came up for Monday but he might be able to get out of it and if not then we should pick another night that week. It seemed like a legitimate excuse and that he really wanted to still get together. I called him back and left a message saying that I was free one night later that week. Then I never heard from him.

::::crickets::::

The next couples of nights I noticed that he continued to log into Match but he wasn't communicating with me. Finally by Wednesday he said that he suddenly got really busy with work and he wasn't going to be able to get together and he hopes I had a good weekend. Um...ok. I know that I don't know what's going on in a total strangers life and there could be plenty of reasons he changed his mind but still had time to log onto Match and look for new people. But the only explanation I can see from my perspective is he had a problem with my voice or he didn't like the message that I left him. I suppose I have a unique voice but it's not that bad. I've actually been told my voice sounds like Gwyneth Paltrow. Nice, right? But that was the only new information that he received about me between planning the date and then suddenly running away.

Obviously I'll never know what was actually going through his head, but this is just another example of how I can't take it personally. We can't help what we're attracted to and what turns us on and off. It made me feel like I really did truly learn this lesson about dating and I'm confident enough that I can just brush it off. Several months ago I would have been completely pissed off or offended. Now I honestly don't care and know that it wasn't meant to be.

Next!

Thanks But No Thanks

I got another text message from the Aviator. He said he was feeling better and how about we get together next week? Um, did you have the plague? I went out with you a month ago. I told him I was busy. If I've learned anything from this entire process of dating is that a flakey personality like that will only end up pissing me off. I don't understand the benefit of stringing somebody along. If he liked me enough to see me again, why doesn't he want to see me sooner rather than later? You really can't be that into me if you are fine going a month before having our second date.

He was a Scorpio. Scorpios are known to string people along for as long as they need to. I don't think I'll be going out with anymore Scorpios anytime soon.

From Russia with Love

I just had an intense few dates with a man from Russia. We went out 3 times in 5 days. I don't know if it was a coincidence or if it's because we are both Geminis but I felt like our brains worked the same way. The conversation never got too personal but we talked a lot about people, religion, politics, and just our world-views in general. Even though we didn't necessarily have the same personalities I could tell during our conversations that we had a lot of the same thoughts. It was a very unique experience to go through and because of that I really enjoyed talking with him.

I was getting a very strong gut feeling though that things wouldn't work out between us. He didn't seem like the kind of guy that was looking for a commitment. Plus even though it's fun having a conversation with somebody very much like myself, and sometimes it can be a good thing having a relationship with somebody with the same kind of brain, I think two of our brains would be too much. I have a hard time dealing with my brain sometimes so I am not necessarily looking to add another one to my life. We are both debaters and argumentative (in a fun, sportful kind of way) and spend a lot of time analyzing situations and people. That screams chaos for a relationship. I didn't have any reason to think that I wouldn't enjoy any future time I spent with him, but I didn't see any cohesion to the time that we would have spent together. I couldn't see a solid relationship with him.

Ultimately, I probably would have been happy giving it more time to see where it could have gone but he was putting a little pressure on me to make a decision. He didn't understand how I could still be hestitating after three dates with him; that should have been more than enough time to know if I wanted things to continue with him. He is completely against the idea of men and women being friends so as soon as he made that clear I felt like it had to be all or nothing. Attraction and dating isn't that clear cut to me. JT and I started out as friends with crushes on each other and we just took things slow and steady. I think if he gave me a couple more dates I probably would have started to ignore my gut feeling and just gone with the flow. I think I could have become very attracted to him if he gave me a little bit more time. Since he didn't, I felt like I had to make a decision and my decision was to walk away.

He has since contacted me saying the door is still open for me in case I change my mind. He is drawn to me in some way and quite honestly I haven't quite been able to shake him from my mind. At this point though I still feel pressure. Like if I reach out to him again then that means we're moving full steam ahead and I am not sure about that still. Even though I could have gotten past my hesitations and ignored my gut, my gut is always right. But there isn't any harm in dating somebody as long as you know going into it that it probably won't last. It could have been a fun experience and a distraction while I continue looking for somebody I could be more serious about. But I just don't do well with pressure. I guess this made me learn that I run from a situation if I am being pressured into it.

I still haven't completely ruled out the idea of seeing him again though. Normally when I end things with somebody it's a relief that I don't have to deal with them anymore. I'm not feeling relieved this time. The idea is still kind of haunting me a little bit and I'm not quite sure what to make of it. I do know if I go down that path though it won't go anywhere and there is potential fo me to get hurt. I guess I am just feeling unsettled with my decision because I don't know if I just chickened out because I'm afraid of dealing with hurt again. I haven't decided yet if I was being smart or just a scaredy-cat.

I am also nagged by my own self-doubt about my potential to find the right person. This was a guy who was completely attracted to all of my qualities that men often find intimidating. I am extremely independent...to the point that it scares a lot of men. They end up thinking that I don't need them. This guy loved this about me. But I am seeing a pattern that this ends up attracting emotionally unavailable men. They see my independence as meaning that I will be OK without having a serious commitment which just isn't true. Even though I don't NEED a relationship or a man in my life, it doesn't mean that I don't want it and that I'm not looking to share my life with somebody. I don't know how to find that balance so I can attract the right guy for me.

Always a bridesmaid...

I know three people who have gotten engaged in this past week alone. Not that I'm keeping score or anything, but a steady stream of Facebook relationship status updates is enough to make me reflect on why other people are finding their partners and I'm not even close. It seems like I'm finally reaching that age where people are getting engaged and settling down a little bit. Prior to this point it seemed like we were all still too young and if I knew somebody getting married at my age it was probably doomed from the start. Now it's just normal.

So I will keep the numbers of dates I've been on directly proportional to the number of friends I have getting engaged. Three friends just got engaged and I've been on 3 dates within that same amount of time. I have another date tonight...so who's next to pop the question?

On the Wings of Love

So the dating continues...

 Match.com has been fruitful in giving me plenty of guys to talk to and to arrange dates. A couple of weekends ago I went out with a guy who is a pilot; We'll call him Aviator. We met for coffee for a couple of hours. Overall it was a nice first date. The conversation was flowing smoothly, he complimented my eyes and my smile, and overall seemed interested and intrigued. He was a very nice guy and seemed laid back, polite, and good looking.

I left the date feeling like it was a nice neutral first date. I wasn't instantly crazy about him (which I think is good because that seems to backfire for me when I feel that way so soon) but I wasn't annoyed or turned off by him. I was genuinely interested in seeing him again. The date ended by him saying he'd like to hang out again and suggested getting drinks one night in the upcoming week. I said that sounded great and we headed off on our separate ways.

When I got home he texted me that he felt like an idiot for not ending the date better. He felt like he should have walked me to my car and given me a hug but he felt like he was never any good at ending dates. I assured him it was fine, first dates are always awkward and nobody ever knows how to end them properly. He thanked me for being so nice about it and said he would be in touch about drinks.

I didn't hear from him until Thursday when he texted me saying he had been sick and he apologized for being MIA. How did drinks the following week sound instead? I told him that would be fine. Today is Monday and this would be the week that we would get together. I haven't heard from him and my cynical approach I now have towards dating is assuming I won't hear from him. If I do...great. If not...no big deal.

If I have learned anything from all my dating escapades the last couple of years is to expect nothing and then just end up being pleasantly surprised. I don't want to be cynical and harsh about it but I feel that is the only approach I can take at this point. I have bee disappointed a lot and when it comes to online dating I don't think it's fair to have expectations for complete and total strangers. Until I get a chance to get to know somebody and see them a few times, I can't expect anything. So all I can do is let him know that I would be interested in seeing him again and then keep on looking. He doesn't owe me anything at this point.

Am I being cynical or am I just being realistic?

Dexter the Texter

Several months ago my mom began gushing about a vendor she met through her work. She would rave to me about how good looking he is (for me...not for herself). I was still dating Reality Steve when she first mentioned him so I didn't think much of it. Shortly after things ended with R.S. he came into my mom's store again and my mom started digging to see if he was married, dating somebody, had children, etc. He was single and expressed interest in meeting me.

He reached out to me on Facebook and we exchanged emails for a few days. My mom was right...he is super hot. He is completely my type - rugged and masculine. My eye always goes to this type of guy but I've never actually dated "my type." I date cute boys, not hot ones. I was kind of excited at the prospect.

We live an hour away from each other so it was a couple of weeks before we could actually meet up. He was just as good looking in person, but on top of it seemed like a really nice guy and had a great sense of humor. We hung out for a few hours and it felt comfortable. The date ended on an awkward note though because while he was expressing interest in seeing me again he said this was really bad timing on his part. He was about to start working 6 days a week for the summer and he was anticipating that he wouldn't have any time to head up to my neck of the woods to see me and put in the effort to start something up. He didn't completely rule out the idea though. I left the date thinking...whatever, if I see him, I see him. If he was looking for an out that would have been it and I'll just wait and see if I hear from him again. Immediately after the date he texted me. From that point on, I have heard from him every single day for two months. But only through text message. We've talked about everything from our backgrounds to how our days are going to full on flirting...through text message.

I was going to be near his town for 4th of July weekend. I told him I would be around. I understood if he wouldn't have time but if he was bored give me a call. He said he'd let me know. I then of course proceeded to get texts from him all weekend, but nothing suggesting that we actually get together. I realized he just wasn't interested and he was probably lonely and/or bored and that's why he enjoyed texting but he didn't want it to be anything real. I saw it for what it was and continued to respond to his texts just as a friend, with the understanding that I probably wouldn't ever see him again but it was entertaining.

One night when he was out and had a couple of drinks he started texting me about how this is such a bad time in his life but he really likes me and thinks I'm great and he wishes we lived closer together so he could have been hanging out with me that night instead of his friends. I told him that I had no idea he felt like that. He responded basically saying, why else would he contact me so much if he wasn't interested in me? I still continue to hear from him everyday but there is no talk of us ever seeing each other, even though he continually hits on me and tells me he finds me attractive. I don't know what he wants from me...but I do know I'm not going to wait around or bug him to find out. He knows where to find me. The whole situation is very bizarre but in some strange way I kind of feel like I've made a really good friend out of it. If I do ever see him again I will already know so much about him and we've bonded over several things. I guess this is what it feels like to have a pen pal.

In the meantime the dating game continues...

Doggone it

So I kind of fell into a side career as a dog walker. I never signed up for it...it just kind of happened. I love dogs so when I moved into my current apartment a couple of years ago my landlords agreed to lower my rent if I walked their dogs a few nights a week. I then had a friend who was heading out of the country for a few weeks and wanted somebody to stay at her house to watch her two dogs. From there it became completely referral based and at one point I was up to 5 clients that needed me whenever they were on vacation.

I had one client that my landlady referred me to. We met in person once but talked on the phone whenever I had to check in with her while I was watching her dog or when she needed to book me for an upcoming weekend. Out of the blue she asked me if I was single and if I would be interested in being set up. Sure enough the set up happened. For reasons too complicated (and quite frankly boring) to explain here, my mom now refers to him as "Reality Steve" so I think it should stick.

Reality Steve and I hit it off right away. We had a great first date. We have similar senses of humor and I thought he was a very funny guy. He was cute...not necessarily my type; but he was definitely a good looking guy. More than anything I loved his sense of humor. I was really impressed that a woman who only met me once could set me  up with somebody that I clicked with. Reality Steve and I dated for two months. Looking back it now seems like a whirlwind. He was full speed ahead most of the time and would randomly slam on the breaks on occasion. He would make jokes about us getting married, make comments about how he could arrange through work to be able to move to my favorite city in the world, and make overall comments about us being together in the future. But he still gave off a vibe of not quite being sure what he wanted. His mixed signals left me feeling paralyzed and neutral. I couldn't get excited about the thought of a future with him when I was still getting signals every once in a while that he wasn't sure. I couldn't totally rule him out and think he wasn't ready because he was showing signs of being very interested. The highs and lows canceled each other out, leaving me feeling something in the middle.

The last week and a half that we were dating he drastically pulled back. Finally one night he called and he said something didn't feel right and he didn't think it would work out. I was honestly pretty pissed. I didn't feel like he gave me a chance. I never felt like I had a chance to let my guard down with the mixed emotions I was feeling. It left me feeling like maybe I did something wrong or I didn't try enough or show him the real me. That's not a good feeling to have after dating somebody. In hind sight, there was something that was slightly off. I really liked his company and again, he made me laugh more than anybody else I'd ever met. But I think we were both having a hard time reading each other and something was missing. It was close...but not entirely right.

After he dumped me we said we wanted to remain friends. We talked a couple of times and only after we broke up did I find out that he was engaged to his ex-girlfriend for all of one week. He proposed and broke it off a week later. That happened pretty much exactly one year before us dating. He blamed his last relationship on him not completely being ready. Finding out what happened I thought he sounded confused and not sure what he wanted and his ups and downs made sense to me. I think he probably feels like he should be settling down and getting married (he is 35 if his age is relevant to this story), but deep down he didn't really feel ready for it.

Lo and behold I heard from him a few weeks later telling me that he started dating somebody and he didn't think a friendship would be possible between us. He considered me a friend and wanted to be on friendly terms, but it wouldn't be possible for us to hang out. He didn't want to have to explain to his new girlfriend that he was hanging out with the last girl he dated. I understood. I also was pretty peeved that I fell for his whole "Oh I'm just not ready" charade. But, overall I was over it. I basically was his rebound girl and that's a tough spot to be in. Even though I tried to avoid it and thought it had been enough time since his ex, I didn't know enough of the details and I ended up falling into that trap. The rebound girl never has a fair chance.

My story of Reality Steve finally came to an end a couple of weeks ago. I hadn't talked to him in about 6 weeks - since he told me about his new girlfriend. He emailed me to say hi and ask how I was doing and to casually mention unenthusiastically that his girlfriend was moving in with him. 1.) They've been dating for two months, tops. 2.) Why the hell did you email me to tell me that???? I was left feeling like he had something to rub in my face. It almost seemed like I was the one that dumped him. You don't dump a girl and then email her out of the blue when you ask your new girlfriend to move in with you. I replied telling him I was great and I was very happy (which is true) and told him I was dating somebody (which is slightly true...I'm dating...just nobody in particular). I also made sure to tell him about a photo shoot I was asked to take part in for a fall fashion edition of a local magazine. His response:

"Classic luck on my part. As soon as I stop dating a girl she ups and launches a career as a fashion model."

You better believe it, Reality Steve.

Tom, Dick, and Harry

So after my long explanation of the history between my ex-boyfriend and I, I think I can continue without being so long-winded. The guys since then haven't been around for nearly as long and the stories aren't as complicated. Again, I've changed the names to conceal identities...and because quite honestly it's fun :^)

Matt: One day my co-worker at the time randomly walked into my office one day asking if I was interested in being set up with somebody. It had been six months since my relationship with JT had ended so I figure it was time to give dating a shot again. Matt and I met up for coffee one afternoon. I think we were instantly attracted to each other. We sat for several hours at the coffee shop and eventually decided to grab dinner and our date continued on. I think in total our first date lasted about 24 hours. We continued to date for about four months. We reached boyfriend/girlfriend status but "I love yous" were never exchanged. I was still numb and grieving the loss of my relationship. His father was terminally ill and that took up a lot of his time and energy. Neither one of us had it in us to give it anymore than we did but I think we were both good for each other at the time and provided a distraction. Eventually I reached a point where I couldn't continue in our pretend relationship anymore without feeling icky so I broke things off. We continued dating for a couple of months after that and then I really called it quits. He and I remained friends and I still talk to him and see him from time to time. I have nothing but good things to say about him. He's good looking, very nice, polite, sweet guy. He just isn't a good match for me.

Whats-his-name: A couple of months after things ended with Matt I decided to give Match.com a try. I had never done any online dating before (I honestly had never dated before...I just kind of naturally met guys and it turned into something). I signed up for three months. I went on a date with Whats-his-name (I really honestly don't even remember his name...this obviously is going to end well). We met at a coffee shop in Cambridge. It was only a matter of time before I had to experience a really bad date in life. Our conversation was not clicking at all so we decided to go for a walk. While we were walking he kept trying to hold my hand. I don't understand what signals I possibly could have been giving him to make him think this was OK. Anybody who knows me knows that I can't pretend to hide my feelings of disinterest in people. Thankfully he eventually got the hint by the end of the date because when we said goodbye he wished me good luck. I came home feeling utterly depressed that I was never going to find anybody; and learned that my relationship experiences up until then had been entirely too easy. I think that was my first indication that this was going to be a journey to find the right one.


Dick: A couple of months later I decided to give eHarmony a shot. Match felt too much like a meat market so I wanted to try having guys picked for me. Nothing really developed until I was matched with Dick. He was my age and seemed very cute. We had a couple of false starts where I was expecting to hear from him at certain times and I didn't, but I would eventually hear from him. I suppose that was my first red flag, but I thought I should give him a chance and not be so quick to judge. Our first date was actually great. We had great chemistry and the conversation was really fascinating. I was definitely attracted to him. At the end of the first date we had already made plans for a second date. We saw each other regularly for about a month and then he disappeared. My initial reaction was to just let it go since I didn't have much time invested but a few different people thought I should at least give him one phone call to find out what happened. So I called and was surprised when he answered. He apologized and said that he was starting to feel like I probably was looking for more than he was at that time. I told him I didn't know what I wanted and I was enjoying dating and I actually had another date lined up for the following weekend. This should have been my second red flag, but unfortunately I was bored and in a rut. I ignored my better judgment and continued dating him simply because it was more fun than staying home alone. All of my friends were in serious relationships at the time and my social life was at a low. We continued dating for another three months. Things certainly never got serious but we continued to go out and have fun and I enjoyed having dates on Saturday nights. Then after a lovely evening at a friend's party and talk about potentially doing something that coming Friday, I never heard from him again. EVER. No explanation. No apology. Nada. I reached out to him a couple of times. The first time immediately when I thought I would be seeing him to make sure he was OK. The second time after I knew he was OK (thanks to his online activity) just to tell him it wasn't cool and all he had to do was say he didn't want to see me anymore. No response. I knew it wasn't going to go anywhere...he was a flake and I wouldn't always hear from him when I was supposed to, and quite honestly every time we said goodbye I had a gut feeling that I wasn't going to hear from him again. Even though I saw it coming though still doesn't make it OK. I was mad for a few months after that one. Lesson seriously learned: It's better to stay home by myself than deal with that crap.

Charles: So the date that I went on when I was simultaneously dating Dick, was with Charles. We met for coffee and the date was OK. He was cute but I wasn't terribly attracted to him. I couldn't help but notice that he seemed to have an excessive amount of saliva in his mouth. I didn't want to be judgmental though so I thought I would get to know him better and agreed to a second date. We went to dinner and drinks. There still wasn't anything horribly wrong but I just wasn't feeling it. A few days later we were talking on the phone and it came up that I have a tattoo. He said "Alright, where is it and what is it of?!?" My dad didn't even have that strong of a reaction when I told him I got one. So me being my charming, sarcastic self told him it was of a giant angel on my entire back. When I laughed and told him the truth that it was small and not visible he said "Oh, well I guess that's OK." Gee, I'm glad you approve. He then started saying some things implying that he didn't understand my last relationship (I think because of the age difference) and was telling me that I might not be ready. It had been two years at this point that we broke up. This was also coming from the guy who only just broke up with his girlfriend 4 months ago and even got a text message from her while we were on our date. I emailed him a couple of days later saying that I didn't think it was going to work out. He responded saying that he thought I was wrong and I should reconsider...that solidified to me that I made the right decision.

Tommy: By this point it is June of 2009. A couple of months had passed since Dick and I ended my eHarmony membership. It was a Friday night and I had nothing exciting to do so I went to the supermarket to pick up things for a party I was attending the next night. I was slowly perusing the ice cream section when I hear a voice say "It looks like you're about to make an incredibly important decision." So Tommy struck up a conversation with me. Everything he asked me about myself he responded to my answer with "Ahhh I love _____!" He was incredibly enthusiastic about everything I had to say. I ended up giving him my card and he began emailing me. He certainly wasn't my type but I felt like being open-minded. How many times have we all heard women say that they didn't like their current boyfriends/husbands when they first met? Who knows what opportunities I was missing out on because I was jumping to conclusions too quickly. So we emailed for a couple of weeks and he suggested we get together. I said we could get coffee as friends, and he agreed. We met for coffee and he was incredibly annoying. He continued to be overly enthusiastic about everything I said. I'm all for getting excited about having things in common with people but this was a little over the top. I gave him a hug goodbye and didn't expect to talk to him again. A week later I got a text message from him asking what I was up to for the night. I said I was at a friend's house playing Scrabble. He responded: "Cool! I love Scrabble!!" That was the end of that.

Wishy-Washy: The summer of 2009 I met up with an old friend, George, for a drink. His friend Wishy-Washy was with him. I had met Wishy-Washy before but never spent much time with him. When I was hanging out with all of these guys on a regular basis, he was in grad school out of state so I only saw him when he was home for holidays. Apparently he had always had a little crush on me. George tried to get something in the works. It never quite panned out though. I only heard of Wishy-Washy's interest through George. And George would suggest times when Wishy and I could go out but then Wishy would never follow through. I know that he's on the shy side so I figure maybe I had to take the reigns so I emailed him and invited him out. He sounded very happy to hear from me and wanted to get together but he had friends coming into town when I suggested and perhaps some other time. I let it go. But then I would get more texts and emails from George about Wishy's interest. Finally one night they were out together and George is communicating for Wishy by sending me text messages. We all agreed that that coming Saturday would work for him and I to go out. I never heard from again. I finally emailed George and told him that they both needed to cut it out. I have no idea if Wishy was ever really interested or if George was trying to push the whole thing onto him. Either way, George apologized for how lame Wishy was and said he wouldn't get involved anymore. He thought it would be a good match but Wishy was being a jerk about it. I haven't heard from Wishy since.

I have since dated one more person but he had a little bit more of an impact on me so I think he deserves a separate entry. It seems appropriate to end at the end of 2009 since that seemed to be a particularly frustrating dating year. Between Dick and Wishy-Washy I seemed to be repelling men and having them running away from me.

How Did I Get Here?

So when you're moving forward and learning, I suppose it is best to first see where it is you came from. How did I end up on this dating spree? I feel like this is the first time in my life that I am actively seeking out a relationship, so lets recap to see what has gone right and what has gone so terribly wrong. *Names have been changed or re-created to protect the innocent and the assholes.

JT: I fell in love for the first time when I was 22 years-old. Before JT there were boys I was interested in or dated or had crushes on, but nothing serious. After graduating from college I got a small studio apartment downtown and I was really convinced that I was meant to live my life by myself. I enjoyed living by myself and I couldn't imagine being in a serious relationship and sharing my life with somebody.

Then we met.

I swear if past lives truly exist, he and I not only knew each other in the last one but the one before that, and the one before that... I have never felt such a connection to anybody in my life.

It was October when we first met and we gradually built up a work-friendship (since we worked together), then an outside-of-work-friendship, and finally a relationship. By February we began dating and by March we were inseparable. I think people saw us as a very unlikely pair; I was 3 inches taller than him and 12 years younger. However, our brains just worked on the same wave-length. We had so much in common, had the same thoughts, and were always on each others minds. I very quickly began spending all of my time at his place so we were practically living together and then working together and commuting together without getting sick of each other. When we spent a few hours apart we were both genuinely happy and excited to see each other again. We were always very aware of each other and very in tune.

Here I was, once guarded and comfortable being alone, head-over-heels in love with somebody. He opened my heart so much, not just in our relationship but to the world around me, as well. I suddenly became more compassionate and more willing to share my emotions. No matter what, I will always be grateful to him for that. I learned from him that I am capable of loving somebody and I do in fact want to share my life with somebody.

After just a few months I officially moved in with him. We lived together very well. We never had fights about our living habits and neither of us had to make many adjustments to begin to cohabit. So what's the problem, right? A few months into things we both got laid off. He continued working on side projects but it took me a long time to find a job. That bond and closeness that we had slowly turned into all I had going on in my life. I didn't have any spare money to be able to go out with my friends, plus we lived outside of the downtown area so it was a pain to go out and meet up with people. I fell into a rut where even if I had an opportunity to go out for the night I wasn't doing enough with my life and I didn't feel like I had anything to contribute to conversations. His projects were slowly deteriorating and he was beginning to bleed money. A year-and-a-half into the relationship we were both going through difficult times individually. My reaction was to charge through and stick it out and we would be a stronger couple on the other side of things. His reaction was to push me away and to deal with things on his own and not want to have the burden of worrying about taking care of me while he was struggling financially.

We started off taking a "break" and I moved out and moved in with my parents on Cape Cod since I still didn't have a job. I was absolutely devastated and heartbroken. We continued talking on a regular basis and whenever I had job interviews in the city I stayed at his place. But it became clear that the "break" wasn't going to end. There was no end in sight to his financial struggles and he wasn't anymore stable in his life for his decision to change. I suddenly had no desire to eat. I physically couldn't bring myself to swallow food. I lost 30 pounds; 20 of which I didn't have to lose. I became a hollow, empty shell just trying to get by each day. I cried several times a day, every single day for months.

Eventually I got a job and moved back to the city on my own and slowly started to rebuild my life. I continued talking to him, desperately wanting to give it another shot. What made it worse was he never said anything to me that convinced me he thought he made the right decision. But he still hesitated at the idea of getting back together. He always made comments about possibly sometime in the future, but he didn't want me waiting around for him while he got his act together.

But eventually he started dating somebody else. He originally referred to her as a rebound but to this day they are still together. I may be justifying in order to make myself feel better, but he has never said anything to make me feel otherwise, but it seems to me he just fell into the new relationship. He wasn't looking for it but she was willing to pursue it and deal with his financial mess and she became a convenience. She also never seemed to ask a whole lot of him. The last I spoke to him she was starting to pressure him to move in together and he doesn't want it. It was just validation for me that he is still confused and doesn't know what he wants in life and it can make me appreciate that he let me go when he did.

I do still talk to him. Sometimes much more regularly than others. We'll go a few months without talking but our brains always find a way to reconnect. We'll both end up thinking of each other at similar times and reach out to each other. I recently dated somebody for a couple of a months and the morning after he and I ended things I got a phone call from JT. I hadn't spoken to him in 4 months and that was the day he chose to call me and check in on me. He has a knack for predicting when I'm upset and reaching out to me. Even though it's been almost three years since we broke up, people will still ask me sometimes if I ever think he and I will end up together. And even though I do still feel an incredible connection with him and I do still love him, I can't ever picture a life with him. I truly feel like he may just be my soul mate, but that's not necessarily a good thing. I really don't think I will ever feel the same way about somebody as I did about him, but I think that's for the best. Our lives were so intertwined with each other that it wasn't healthy and I am not sure we would ever be successful at having a relationship without be codependent. The fact that we are still in contact with each other proves that. We've never been able to completely say goodbye to each other. It's gotten to the point where it's a big, unhealthy mess; his girlfriend hates me (and I can't blame her) so he's not allowed to talk to me even though we don't talk about anything inappropriate and nothing physical has happened between us for years. But he does anyway...he just hides it from her. So that makes me feel sketchy and I try to create distance from him. But it's really hard to completely cut off somebody who understands you more than anybody else you've ever met. But I can't see how we can ever have any sort of healthy communication with each other for as long as he is in this relationship. He never allowed himself to get over me because he moved onto the next thing very quickly and it has created unnecessary stress in his current relationship and places a burden on me.

There were so many lessons I learned from him. It took me so so so long to rebuild my life after him. All I wanted from him for a long long time was closure. I felt like I just needed to hear from him that he never sees it working out between us but he has never been able to say it. I finally learned that I wasn't going to get closure from him and I had to create it myself. I was waiting for him to say he didn't think we would work out but I finally have reached a point where I can say that I can't ever see it working. It took me two-and-a-half years but I can finally say it truthfully.

I suppose that since this was the most significant relationship in my life it deserves its own entry. I will save my dating experiences since JT for another entry.

Southern Hospitality

So my new adventure began with a date last night with a self-proclaimed "Southern Gentleman." We met and communicated through Chemistry.com (this was my first time using this site after trying the likes of eHarmony). His eclectic background intrigued me...he grew up in the south but had spent several years living overseas and has been settled in the Boston area for the last few years.

When we both arrived I think we were both pleasantly pleased with each others' physical appearances. He was nice and tall and very good looking. He certainly had the southern charm going on; holding doors open, taking off my coat, and pulling the chair out for me. On the surface everything seemed to be going just fine. Our conversation was pleasant, we laughed at each others jokes, and we seemed to have quite a bit in common. Chemistry is a funny thing though (the feeling...not the website). I couldn't help but feel that I was auditioning for him. He didn't seem the least bit concerned how I felt about him...it was all about if I fit into what he was looking for.

It didn't dawn on me until the end of the date when things seemed to end very abruptly that I might not have passed his test. We left the bar and said goodnight, neither of us indicating that we would like to see each other again. But as a girl who has faced a lot of rejection in the last two years, I was more worried about why he didn't seem to like me; why wasn't I what he was looking for? I replayed parts of the conversation in my head thinking what I could have said that was wrong. After 12 hours of over analyzing (11 1/2 hours too many), I realized that I should be evaluating the date based on what I felt about him and if I would want to see him again.

And the funny thing is, I really couldn't picture this guy in my life in any way. While spending only 3 hours with him I already felt the sense that he was looking for a "perfect" woman and that would be way too much pressure for me to feel "on" all the time. I couldn't picture him interacting with some of my friends, going to a hole-in-the-wall restaurant to grab dinner, or to go see a live show at a local dive bar. I couldn't pictures his shiny, new expensive car sitting in my driveway while we hung out in my quaint little apartment for an evening. And as much as I like sophistication and culture and have an eye for the finer things in life, it's not exciting enough for me to do everyday. I like variety. I am adaptable and like to mix things up and be in different environments. Quite honestly, he was a little too snooty for me.

So lesson #1 was a valuable one. I need to stop evaluating dates based on whether or not the guy ends up liking me. Obviously it's important if I really am interested in a 2nd date that the guy finds me likable. But I need to try to see beyond whether or not he has a cute smile or nice eyes to see how I feel, see if there is enough there for me to want to learn more. If I had listened to my own head at the end of the date I would have walked away seeing it for what it was - a nice evening out having pleasant conversation over a glass of wine - and saved myself a few hours of agonizing about what I am doing wrong in the dating world. Hopefully I will remember this lesson after the next date I go on.

Hello there!

Dating. It's a tricky thing. But who doesn't know that already? This certainly isn't the first blog dedicated to navigating the dating pool...not even the first one dedicated to dating specifically in the Boston area. It is my way though of navigating my own mind and experiences, and perhaps somebody will stumble upon this that can relate or contribute their own insights and experiences.


After a solid two years of stalling and false starts, I have been dating on and off and coming up short. All in all, I think I am just flat out bad at dating. When you think about it, dating is really like a job interview. You have a short period of time to show somebody what you would be like in a relationship. I don't think I give an accurate depiction to what a life with me would be like. After a few bad experiences and dating a few jerks, I have become guarded and hard to read. Who wants to make a commitment to that girl, right? And even though I am aware of this problem, I can't seem to quite shake it. It's hard, however, to improve on these things when I am only going on a date every few months. That is why I am setting out to date as much as possible, simply for the sake of practice.


Stay tuned as I begin this new journey and hopefully learn an awful lot about myself in the process.