Love is a Gamble: To Three or Not to Three

Dear Addy,

I am a bi-curious guy in a weird situation. I have been friends with Cool Dude for many years during which he has gotten married and started a family with Sexy Chick. The three of us get along quite well. Recently, our gatherings have shifted in tone: After several bottles of wine, Sexy Chick starts to openly hit on me in front of my friend. She basically invited me into a three-way with the two of them. My buddy seems to be interested in this arrangement too. Up until this point I’ve turned her down.

Here’s the issue: While I am definitely interested in exploring the less traditional aspects of my sexuality, I don’t know whether it would be a good idea in this particular case. I’m not entirely comfortable with the fact that we’re all such close friends, plus I don’t like the idea of a wet and wild threesome when there are young children sleeping down the hall. Should I say yes, on the condition that we go someplace safe like a hotel?

Sincerely,

You & Me & The Bottle Makes Three

Dear You & Me,

The first thing I notice about your letter isn’t ZOMG HOT SEXY THREESOME (!!!) – it’s Hesitation, with a capital H. That should be the first sign that this isn’t a good idea. Regardless of what any stupid advice columnist will tell you, your gut is one of the best decision-making tools you have. And if your gut is telling you this isn’t a great idea then perhaps in this case it’s best to listen.

Listen, I’m not the type of gal to go around bashing the idea of a threesome. In my opinion, they’re sort of like chocolate-lava cake: Very delicious and decadent, but not something to be routinely indulged lest they lose their appeal. Dessert metaphors aside, I think that group-sex activities are best practiced with those you don’t already have a long-standing friendship with. Unless you plan on entering some sort of polygamous co-relationship with these two, best to find your jollies elsewhere. Having casual sex with a married couple with whom you are already close friends can lead to a number of possible scenarios, many of them being awkward and friendship-dissolving.

Let’s also consider your needs in this situation: Are you even attracted to your (male) friend? It sounds like the wife is the one putting on most of the pressure. Remember: Just because someone’s offering up booty on a platter doesn’t mean you have to say yes. (Wow, never thought I’d type that sentence with a straight face…)

Do people hook up with their married friends over bottles of wine and have great times doing so? Of course. Do I think you should explore your bi-curiosity? Most definitely. Do I think you should avoid a potentially sticky situation that could cost you your friendship with this couple? Yeah, I think it’s for the best. I don’t think you’re wavering because there are “children sleeping down the hall” (which, ew) but because deep-down you’re trying to spare yourself the confusion and controversy that comes after your best friend’s wife gobbles your junk and likes it a little too much.

If you’re interested in exploring your naughty boy-curious side, try a free dating site chock full of like-minded gents such as OKCupid.

Bonne chance!

Got a dating/relationship/sexy question that needs answering? LoveIsAGambleTFT@gmail.com

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