Ask Minda Honey: How Do I Date a Guy If I’ve Been Sleeping with His Friend?

Jun 5, 2019 at 9:57 am
Minda Honey

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Hey Minda!

Soo, Louisville is a small town, like super small. Either you were born here or went to college here or you are a transplant. Well, I’m two of the three. I’m a transplant and went to school here. I’ve been casually having sex with this guy for two years, nothing serious. We never clicked. When he talked, I heard whomp-whomp-whomp, but I didn’t want to be giving my cookie to everyone, and it was decent. Well, last December, I met this guy while I was out, but I had already been crushing on him before I met him because I knew of him through social media. So, recently, he and I started talking and getting to know each other. I really like him and think things could really flourish. So, my issue is, he and the guy I’ve been casually having sex with are friends. Like friends friends. Should I tell the new guy about me having causal sex with his friend, or should I wait and hope that he never says anything? Help! I’ve been single for a while and I’ve finally found someone I really like! Thoughts?

Sincerely, If this doesn’t work, I’m getting a sugar daddy


Start looking for that sugar daddy!

I’m for real over here struggling to do the algebra on your situation because there’s too many damn variables. This is one of those scenarios where the advice I want to give you probably isn’t what I’d actually do. Relationship Advice Minda is like, yes, you need to be transparent, honest and upfront about this scenario with both men.

But 30-plus Minda with her fishing rod cast out on Louisville’s shallow, often fetid dating pool would hate to lose a potential catch because she did what she had to do to keep her bed toasty these past couple of years. I’ve had to level up in emotional maturity since I moved back home because, unlike in LA where failed-dates disappear from your life, in Louisville you’re going to see that person you smashed once, twice, a dozen times. You’ll run into them at your favorite bar. Outside of your accountant’s office. With their latest partner. With your latest partner. Y’all gonna see each other. My polite grin game is now on a thousand trillion.

So, let’s talk about the variables. You weren’t on any sneak shit. You didn’t know Mr. In-The-Meantime would be pals with Mr. Right. So, you can’t be accused of doing anything grimy. I can’t even fault you for sleeping with someone “decent” in bed for years because “one in the hand is better than two in the bush,” doesn’t just apply to birds. Why risk the disappointing, when the mediocre is at least reliable?

What we don’t know, and what you don’t even bring up, is maybe these two have already talked it over. If this dude just casually slept with you for two years without attempting to gain any forward momentum, he might not be that attached to you, and it isn’t anything for him to step aside and let someone with true love potential come through. If they haven’t talked about it, do you think he’d stay quiet about it or be petty and let his partner know what’s up? Would the guy you’re actually into be turned off if he knew you slept with his friend? Some dudes have a major issue with this, and others are willing to let it slide because they’re struggling to tread water in the same tiny-ass dating pool. If no one tells him, and he finds out somehow further down the line, will he be more or less upset about this information? And if you do decide you should tell him, how do you even go about that? When is the appropriate time to let that truth bomb drop? And do you owe your casual thing a courtesy notice that you’re pursuing his bro? I just don’t even know.

I think ethically, you’re not obligated to share your sexual history with anyone as long as you’ve been making safe choices and aren’t exposing them to anything or jeopardizing their health. But at the same time, I know I’d want to know if a guy had slept with a close friend of mine, especially if it was recently and regularly. And I’d want to be sure that friend wasn’t going to present a problem in our union – and that’s if I was into this person enough to even want to deal with that complication.

I don’t think there’s a way to make this less complicated. I suggest getting to know the new guy a little bit better. It might end up being a non-issue if you all don’t actually click. If you do, you can broach the topic the same way you started your letter, “Louisville is so small, it feels like everyone has dated everyone … ” And just see where the convo goes. Maybe he’ll reveal he’s banged your bestie, and y’all can call it even. Either way, get going on that sugar daddy research. —Minda