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Two Sense: Should I Let My Feelings Get the Best of Me?

A year ago, I met "Michael" on an online dating site. Given that I had recently divorced, I took my time with him. But after four months, I was surprised to learn that he was not developing romantic feelings for me. Because I cared for him and enjoyed our friendship though, we embarked on a "friends with benefits" relationship: sexual monogamy with the understanding that we both wanted more from a partner eventually. For the next eight months, we spent about a third of our time together, during which I constantly waged war against my growing feelings toward him. This past Thanksgiving when Michael went to see his family without me, I felt literally left behind, and began actively dating. I met someone who is totally into me. I told Michael, and we agreed to just be friends. But two weeks later, Michael began sending me affectionate messages, and last weekend, he disclosed that he did have feelings for me. I adore Michael; I dare say I love him. I’m scared of being hurt, but at the end of the day, being with him feels right. Do I throw the proverbial caution into the wind?

He Said: I sometimes (read: all the time) use a gay dating (read: hookup) site called Adam4Adam. It is composed of page after page of tiny square photos of local men of all ages and colors marketing their desirability. What's actually more interesting, at least on an intellectual level, is the sociology of the mating dance among members. Basically, if you show too much interest in a guy, he suddenly becomes hard to get. But if you ignore his advances, his enthusiasm for getting together soars. This is what happens to human beings when there is an abundance of possibilities—we are always looking for something better in the proverbial next square, even if it's illusory.

This, I fear, is Michael's problem. You gave him plenty of opportunity to allow your dating to flower into a fully romantic relationship, and he flat-out declined. In fact, he designed a dating program ripped from the pages of Adam4Adam to make an emotional attachment all but impossible. And he only became more engaged when you were on the cusp of moving on. Since you are the more emotionally forthright person in the relationship, you are right to be scared. At this point, I'd limit my vulnerability by continuing to date the other guy, and indicate to Michael that while you care about him, he really needs to woo you. Not as part of an Adam-style game, but because he needs to show that he means it, and that you mean that much to him. Good luck!

She Said: After a year of sleeping together, during which Michael displayed no sense of commitment, he discloses that he “has feelings for you” only after you dump him? I’d like you to think back and focus on the exact words of this disclosure. Were they something like, “I realize I’m in love with you and I want us to be completely monogamous and pursue a serious partnership,” or were they more like, “I guess I do have stronger feelings for you than I thought” or “I’m still ambivalent about a serious relationship, but I miss you”? Be brutally honest. Only if Michael’s profession of romantic feelings was deep and total would I even entertain the possibility of seeing him again. And even so, proceed with caution. See if his actions match those words: if he initiates contact, makes you a priority, introduces you to family and friends.

If, on the other hand, his “affectionate” advances were anything less than zealous, you are right to back off and stay away. For there can only be three possible objective truths at play here. (1) Michael has had a deep realization of the worth of your relationship, and the circumstances that initially made him lukewarm (perhaps he was still reeling from a past relationship, for instance, or your time together has softened him), have passed. (2) Michael simply does not have a strong, organic sexual attraction to you, but he cares for you and is loath to let you go. (3) Michael only wants what he cannot have, and doesn’t want it once he has it. The only way you want to continue a relationship with him is in the first case. Don’t be tempted by anything less. Listen carefully to his words and watch his actions to determine if his feelings are anywhere near as deep as yours. If not, you’re wise to stay away. In time, you’ll find a man who thinks the sun rises and sets on you. That’s the kind of man a thoughtful, articulate, open-hearted woman like you deserves.

“He” is Chris Bull, author of seven books, editorial director of Queerty.com and cofounder of GayCities.com.

“She” is Robin Rinaldi, 7x7’s former executive editor, currently at work on a memoir titled  The Wild Oats Project.