Q: I went on a date with my best friend because he told me that his feelings toward me had developed more. The date wasn’t a disaster, but the bedroom was. We laughed about it after—even a little bit during—but this might be a deal breaker for me. He says we should just try again, but I’m thinking: We already have the greatest friendship in the world, so why try to add sex to it if it’s just going to get awkward? Should I risk hurting his feelings and telling him we should stop now? Or keep at the sex, hoping it gets better? I like and love him, but I’m not sure it’s worth losing our five-year friendship if it doesn’t work out. Ruben via instinctmagazine.com
A: I can tell this is important to you because your strong emotions have boxed you into some false either-or dualities. For instance, you can either be friends or lovers. Oh, really? Not both? Or some kind of interesting mix? Another false duality you hold is that either the sex will turn into a love affair or the friendship will be destroyed. Oh, come on! You’re best friends; you can forgive each other for shooting for a little more out of life. Dare to see what happens. The key here is for both of you to be honest and open with each other about your feelings. It’s very encouraging that you laughed about the not-so-hot sex afterward and “even a little bit during.” Wherever you guys end up, I don’t see either one of you unfriending the other on Facebook.
IT AIN’T OVER ‘TIL IT’S OVER Q: Can you ever really get over your first true love? I thought I had, but I think of him often and “spy” on him on Facebook sometimes to check up on him. My current beau says that I’ve muttered his name in my sleep (which I’m not sure is true, but it could be true) on more than one occasion. I know no surefire way to cleanse him from my memory for good. Do you? Howie via instinctmagazine.com
A: I answered a similar question just a couple of months back in my February column. You were probably too busy cyberstalking your ex to notice, so here it is again. It. Takes. Time. Time you didn’t give yourself because here you are in another relationship still mooning over the man that got away. You’re so busy wondering what your ex is doing that you’re not able to be fully present to the man you’re with now. Howie, I hope you’re hung, because that’s about all you have that’s really available to Mr. Current Beau. For the rest of you readers following along, look at this situation and don’t let it happen to you! After a breakup, make damn sure you’re over the last guy before you wrap your lips around the next. Otherwise it’s emotionally unhealthy for you and totally unfair to the new man, so how long do you think that’s gonna last? Yeah. But I do have one last nugget for Howie—if you’re still wanting a way to cleanse your “first true love” from your memory, get this: If you’re not together now, he wasn’t your true love. Start there.
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MAN, OH, MAN! Q: I’m not sure how to ask this without sounding like a self-hating homo, homophobe or worse. A guy has been flirting with me at the gym. While I was once reasonably attracted to him, I learned that he was formerly a woman, and any attraction I once had went away. He’s transgender (female to male), and that has me skittish about dating him, but I don’t know how to tell him I’m no longer interested. I don’t want to offend him, but I’m not sure honesty is the best policy here. Jesse via instinctmagazine.com
A: Let’s all stop beating ourselves up for not always having the newest politically correct response at our fingertips or in our pants. I get that you want to do the right thing by this new man, and kudos to you for it. But a person will either make your dick jump or he won’t. That’s not judgment, that’s just what turns you on or leaves you limp—whether it’s a guy at the gym, the thought of a little bondage or a pair of Prada shoes. I’d suggest you remain friendly and smile, but let it end there. If he asks for more, he deserves the same kind of honesty you’d give to any other man you’ve flirted with but didn’t want to bed. A sweet and sincere “No, but thanks for asking” will do fine. Trust me, there’s somebody out there who will pop a chubby for this guy—that’s the beauty of this crazy-diverse world. It just isn’t you. Or at least…not today.
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