Ask Mom & Spawn: How do I turn secret vacation sex with a friend into a relationship?
“I recently went traveling with someone I only saw as a friend. We started sleeping together and spent the end of the vacation as a couple. As we have a lot of close mutual friends, we decided none of them could find out. Now that we’re home, we pretend like that holiday was nothing special, but I now have feelings for him and am not sure I want to make the first move. We talk to each other a lot more than we used to and have gone out for drinks just the two of us, but there has been no physical contact since we’ve come home…not sure what to do.” – Anonymous
@CrazyJewishMom: Are you serious? ATTACK HIS FACE!! What’s confusing here?
@KateFriedmanSiegel: Please don’t.
@CrazyJewishMom: What’s the problem? Just go for it! What’s the worst thing that can happen?
@KateFriedmanSiegel: She could destroy an important friendship!
@CrazyJewishMom: Honey, you’ve made eye contact with his penis. If a little manmeat was going to destroy the friendship, it’s already over.
@KateFriedmanSiegel: That may be fair.
@CrazyJewishMom: The sex bell has already been rung, so what do you have to lose? GO FOR IT, but be prepared for rejection, it’s not a good sign that he isn’t making moves on you. At the beginning, you should be so infatuated with each other that you have to sneak into public bathrooms to scratch the sex itch.
@KateFriedmanSiegel: Dear god, I hope you never did that. Also, I disagree – just because he isn’t having itchy, public bathroom sex with you doesn’t mean he isn’t interested. It really depends on how close you were as friends before you started bumping your parts together. He could just genuinely be trying to respect your boundaries and be worried about the same things you are. Regardless of how he feels, you like him so, I agree with my mom, you probably can’t just ignore that. Friendship can be a great foundation for a relationship, and you’ll always wonder what if!
@CrazyJewishMom: See? I’m right. Unzip his pants.
@KateFriedmanSiegel: Or you could try a slightly less direct approach? Maybe go for a drink and bring up the fact that you had a lot of fun on vacation with him! Hopefully, it will naturally transition to sex, but if he’s cagey, directly tell him that you’d be up for trying it out IRL.
@CrazyJewishMom: I’d go for the crotch, but however you do it don’t worry. Even if he rejects you, there’s plenty of manmeat at the butcher. And if he’s really a good friend, you’ll get past it.
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