This is a little long, I apologize, but I find myself in a bit of a pickle. I am usually the one doling out the advice but I find myself at a loss when it comes to me. A little about myself: I’m a 27-yr-old looking to go back for her Masters, fun, energetic, athletic, fabulously awkward and mildly attractive laid back woman who still has managed to keep (some of) her sanity even though I’ve never had a true relationship because I literally date the worse men for me: uneducated, selfish, drunk, irresponsible, obsessive jerks.
The end of May last year one fateful Saturday night, I met this well-dressed, educated, gainfully employed gentleman (and a nerd, God I love nerds) at a bar. I was a wee bit tipsy, but we engaged in good conversation and exchanged numbers and a kiss. To my surprise he rang me that Monday. Being the sane woman I am, I did not answer, I hate talking on the phone. So, after waiting until the next evening to text him back-stating that I had left my phone on silent and missed his call and he stated he was interested in seeing me again. We made plans for a rendezvous later that Saturday. Had one of those first dates you see in the corny romantic comedies that last from the afternoon until the wee hours of the morning. The painful shyness (more so on my part) and the spilled drink on the shirt (again my part) but great conversation. Then the beautiful disarming sweet good night kiss. I was hooked.
We proceeded to see each other a few more times when he drops the bombshell on me: he wants to get married and have kids soon, his little biological clock was ticking. I thought nothing of it at the time and we had 2 more dates after that then I finally let him seal the deal. Apparently, sleeping together made things too real and he needed something more substantial, more serious. Which was the problem, in his eyes. We have a bit of an age difference (8 ¾ years difference to be exact) and he has it set his mind that since he did not want to be in my position when he was my age, that I certainly would not want to go down that road with him. I could not promise him that I would be ready in a year to get married and that it was not fair for him to keep seeing me. So we parted ways, promising to still be friends. But we still saw each other regularly and continued to sleep together … for five months. We still discussed things like what we both hoped for, individually, in the future. Almost completely in sync, if I were maybe two or three years older. Problem was, as we spoke I began to realize that I had never been this honest with another man nor managed to bag anyone even close to his caliber and the reality was as much as I was terrified of the thought of that type of commitment, I do want to be married before 30 and I’ve only got a few years left before that mark.
Finally, I told him how I felt: that I really cared about him and wanted more from the arrangement. He proceeds to tell me that he had no idea that I felt that way and he had not thought of me in the same way since he told me that he could not date me anymore. He gave a decent explanation: we are at different points in our lives, I still need to discover what I truly want to do, and he doesn’t want to hold me back. Crushed and licking my wounds we vowed to be friends but not see each other for a while to avoid falling into the same old pattern of me winding up in his bed after spending time together. Fast forward four months later: we had still stayed in contact via text and the occasional email but then one day I had a day off and suggested we meet up for lunch. Circumstances prevented us from meeting up until dinner time. The same old routine happened again. But something had changed, he spoke of women older than me and how they were not interested in commitment and how his friends think he should date younger. A glimmer of hope for me, possibly? So here I am again, just little more figured out career wise and a few months older but still lost in his eyes.

– Floating and Confused, Cape