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.