Meredith,
I am a pretty regular reader of Love Letters, probably because I believe strongly in love, would love to find it and love that I’m not the only one.
Ok, to my current issue: I am 28 years old. I am very successful at work, have an amazing family and friends, I’ve got a great face, an average body, a fantastic personality and a ton of life. I was overweight growing up and as a result was every guy’s best friend. I’ve lost that weight and have been on the dating scene for the last few years trying to make it work. A bit more background… I am 100% against settling and have this vision of the real, great and big love; therefore I’ve dated plenty of guys five to six times and realized they just weren’t setting my world on fire and dropped it. This might be part of my problem.
In the summer I met this guy. Our first date last five hours and we never looked back. I immediately was connected to him and our conversations were deep, interesting, funny, and real. He became the most important person in my life, quickly. He is inherently a selfish individual and leads a pretty secluded life (entrepreneur, works from home, family lives out of state), however, he let me in 100 percent. There was a ton of passion, a ton of arguments, a lot of tears, and a lot of learning about how to succeed (and fail) in a relationship. We ended up parting ways in November, mostly because he retreated into his shell after one particular argument and made a decision to not come out. I had also had enough and KNEW I deserved to be treated much better. We haven’t talked for a few months, much to the joy of my friends, and I have been attempting to move on. I’ve had another two runs at the five-six date guys who have all been really nice. Much nicer than summer boy, however for some reason, none even compare. We recently started e-mailing again and have been discussing a possible dinner get together.
SO to my question… Am I just clinging to summer boy because he is the first guy who has been able to keep up with me, challenge me and inspire me… or am I clinging to him because he is the only one I’ve ever loved? Do I take the string of five-six’ers as a sign that he was more than that or as a sign that I’m looking for the wrong thing? Is it possible to try again and have it be different? I don’t know if I should even open Pandora’s box and go to dinner or just walk away completely…

– Wanting the Whole Enchilada, Boston