Savage Love: Gayed, Blacked, Transgendered

Navigating a language minefield.

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I’m a 37-year-old straight male and I’ve never had a girlfriend. I lost my virginity when I was 25 and proceeded to have sex with dozens of women over the next five years, but none lasted more than a night or two. Over the next few years, I dated with the goal of finding a relationship, not sex, and found neither, then a few years of depression. The question is: Am I screwed? Will women my age be willing to date someone with no relationship experience? Is it something I should be up front about?
Hope Over Personal Experience

There are tons of women your age who have similar dating histories — there are tons of women your age with no dating histories at all — and you won’t be at a disadvantage, experience-wise, if you’re willing to date one (or more) of them. Create a few online personal profiles, HOPE, and be up front, honest, and unapologetic about your dating history and your desire for a relationship. State that you are looking for a woman understanding enough to look past your inexperience and offer that you are willing and able to do the same. Good luck.

Any tips on getting over unrequited love? I’m a 30-year-old straight male who fell in love with a girl who didn’t want to proceed with a relationship. I have tried the gym, movies, socializing, and dating other women, but I still can’t get her off my mind. To make matters worse, I will be running into her a lot in a professional setting in a few months. It has been 1.5 years, and I still haven’t gotten over her. I fear that my future interaction with her will make it impossible to move on.
She Moved On

For two years, I pined for a guy I couldn’t have, certain I would never get over him. So I called him one day and asked him to have lunch. The plan: throw myself at him and convince him to leave his boyfriend for me. Failing that, convince him to resume cheating on his boyfriend with me. But five minutes into lunch, I realized I wasn’t attracted to him anymore. It wasn’t that I couldn’t get over him during those two years, SMO, but that my ego wouldn’t let me get over being dumped. With that realization, the spell broke. We ate our sandwiches and said our good-byes. Maybe you’ll have the same spell-breaking experience when you run into this woman in a professional setting? If not, keep trying the gym, movies, dating, etc. until the spell breaks or your life ends, whichever comes first.

Follow Shadi Petosky on Twitter @shadipetosky.

On the Savage Lovecast, family law for the polyamorous: savagelovecast.com.

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