Alias (DO NOT USE A REAL NAME!!): Living Sideways
Comment: I met “Jan” as a classmate in university in the 90’s. She always made lots of sexual innuendo in her conversations with me and my male friends and often talked about the kind of sex she was interested in trying. That always turned me on. She was dating some guy at the time, but she was not happy about the relationship. They broke up a few years later. By then, I had moved out of town, but I came back into town often to visit to catch up with friends and former classmates. During a couple of my visits back, “Jan” and I went on a couple of dates. On our first date, she said to me that she was “fuckable” three times. I wasn’t sure if she wanted to get things on with me or not, but I got the feeling she was interested in a relationship. We never took things further. She came across as ambiguous when we parted, and I am sure this was also due to her many insecurities. Also, my career was taking off while she looked like she was stuck in a dead-end job and lifestyle. She didn’t share my ambitiousness in life and my outlook for the future. Fast forward fifteen years to 2012: I came back into town for a few days and “Jan” and I went out for lunch. I found out that she was indeed still rotating through the same dead-end jobs and her lifestyle had not grown beyond the small town where she lived. We are both still single. Now I am back in town again for a few days and reminiscing a lot. Having had a lot of non-starter relationships in the past, I am thinking that I should have dated “Jan” back then. If I knew what I know now, I would have given it a go. It’s too late now to follow up. We live and work thousands of miles apart and have different lives. But I feel like sending her an email to tell her my thoughts and that I was always attracted o her sexuality, her love of travel and her athleticism. Would an email like this put her off? What should I say or not say that would make it better received?
City: Niagara Falls
I suppose much of this depends on your end goal. What are you hoping to achieve by telling this woman that you found her sexuality appealing twenty years ago?
For the record, telling a woman you’re attracted to her sexuality is not the same as telling her you’re attracted to her. Nothing makes a guy sound more pathetic than when he says something like, “I was always so turned on by the way you talked about sex.” Know what that’s pathetic? Because savvy and experienced people know that the men and women who talk about how much they LOVE sex or how much money they have do so because they feel like they have to. Talk like that is a sign of insecurity. You could certainly write her and say that you regret not pursuing anything with her, but leave out the stuff about her sexuality.
I can’t say that I’d be all that flattered by a man who said he was attracted to my athleticism or love of travel. I mean, thanks…I guess? What do those two things have to do with her personality and character? Those are the aspects of a person that you should be drawn to, not the fact that she likes to work out or add stamps to her passport.
Honestly? This whole thing is freaking weird, man. It feels like you’re getting up there in age and struggle to meet women and so you’re recycling long ago flirtations because you don’t have other options. Making this feel especially off is how you describe her as being stuck in a dead end job and not doing much with her life. It’s as if you think she might be juuuust desperate enough to get with you.
My advice to you is to figure out why you have so many “non-starter” relationships, focus your energies on women in your local area, and forget about this woman from the good ‘ol days.