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.