Sleeping with a Friend


A friend and I recently had a conversation about the possibility of her starting up a relationship with a good male friend she’d had for a number of years. They had practically been dating for years, with dinners, weekend outings and even a few shared nights in the same hotel room & bed. Their kids were even close friends. They had one drunken kiss, but nothing else had ever happened. She asked me my opinion as she waffled back and forth whether or not she could see him in that way, meaning romantic.

This is an interesting one for me, because I probably have as many male friends as I do female. Plus there is the whole, “Been there – done that” vibe going on.

If I wasn’t writing a lengthy blog piece and had to give a quick simple, shoot-from-the-hip kinda answer, I’d say Don’t do it.  That would be without weighing any of the pros or cons, and basing it 1000% on my experiences. But of course every picture paints a different story, and I am certain for others there have been fantastic results. The friend in question had in my opinion, a few additional criteria’s for this situation.

The few times I myself have jumped into this wading pool, the results have varied, but as my current single status shows, it apparently has not worked long term. There are some pros to it, but they tend to be so very murky, that the cons usually weigh them out. Here goes:

  • You’re already know one another

Pros:This is the biggest advantage. You don’t need to go thru any of the rings of fire-y dating hell to meet someone. No Apps, or websites. No wondering if they will like your picture, only to find that they hate your ass. No issues with seeing they are 4” shorter than they claimed. No meeting a stranger that you have to be on your best behavior with. You already know you have some sort of connection, because why else would you be friends? You have some common interests – maybe even more than you would with someone you met online, because you’re already doing those things with each other.

Cons:You know each other, but how well? There is a slight shift in the universe between friend-Me, and Relationship-Me. While all the good of Friend-Me is there inside Relationship-Me, not all the stuff I have in Relationship-Me is there in Friend-Me. Confused yet? Let’s say, we are supposed to meet to get a drink, or go hear a band and you have to cancel at the last minute? Friend-Me is okay with that. I might be bummed at the shift of plans, but that’s about it. You can text me hours before and say you’re sorry but you have to bail on the plans for tonite and you hope I understand. I do. Relationship-Me is going to be a heck of a lot more bummed, because I was probably really looking forward to this time with you. And that text that Friend-Me is okay with? It really isn’t going to fly for Relationship-Me.In a nutshell, the stakes are a little higher, The behavior has to go up a notch, because feelings are now precedent.

  • FWB

Pros: Well sex for starters. You probably know some of the kinks (yay) and quirks (could be nay) about one another if you’re a friend of mine. One of the reasons I love having men as friends is that from time to time the inner Frat Boy in me gets to come out; Anything on a raunchy level can be talked about, including the freaky situations that may have occurred in a past life. That’s not to say with my girlfriends we don’t get as graphic, it’s just a different level. Anyway, having that baseline, only makes sex with a friend fun. All sex should be fun, but good sex really needs it. Which leads to the con of…

Cons: Bad sex. Maybe your connection with one another is fantastic, but once you slide between the sheets something shifts. That is The. Worst. For one, bad sex sucks. For another, you can’t call or text that friend and let him know what an absolute lousy lay you just experienced, because he is both that friend and that lousy lay. The friendship may rebound on the off chance that enough time goes by and you can laugh about it. But if it’s bad because now you know he cries when he orgasms, or worse yet equipment issues on either side of the gender – the friendship is never going to be the same. You’ll always know, and they will always know that you know.

  • Best Friends/Failed Friends

Pros:I think every relationship should be based on being with your best friend. Your absolute best friend, where gender lines mean nothing. I still think a guy should have a guy-bestie and a girl should have a girl-bestie, but relationship besties are the best. It’s probably the one thing I mourned losing the most in my last relationship. We could tell each other everything, and our sense of humour was so similar that we could laugh about things others wouldn’t get. You get that now. Your best friend on all levels.

Cons: Losing that. Losing a tight friendship can be as devastating as a losing a love interest. I am nowhere in the mind-frame to lose both.

  • Possessiveness

Pros:I really find nothing pro about possessiveness, unless it’s in a growly sexual context with the right person.

Cons:Once I have sex with you, I do feel a sense of familiarity that extends itself out a bit to the word possessive. This could (and did) damage things when a failed FWB moved forward into his new relationship and I was relegated back to the best friend status again. It was a hierarchy situation for me, more than an emotional one, as he and I were one of the few situations that moved backwards with initial success. I did not like the demotion, although I did not want the relationship either. The friendship eventually just flapped in the wind until we both called Uncle and walked away from it.

  • The Friendship is Never the Same

Pros:If the relationship were to work out, I guess this would be a good thing. But…

Cons:… if the relationship were to fail, going backwards to friends is rare. Life isn’t a Seinfeld episode and we can’t all be Jerry & Elaine. More often than not, one still has residual emotion lurking about, which can lead to awkwardness.

This isn’t to say it never works. It has and it can. Sometimes, if the timing is right you can slide right back into your original positions, as if the thought of sex or romance had never been in the air.

A male friend and I had an argument once whether the opposite sex could be friends if one wasn’t interested in sleeping with the other. I adamantly stood on the side that said they absolutely could. He obviously stood on the other side of that argument and said men are only friends with women they eventually want to poke. It eventually dawned on me that him telling me this, was him telling me this. (sometimes it takes a brick to fall on my head) and a year later, guess who was right? Did he put the idea in my head, or was it already there and I didn’t know acknowledge it during the argument? It’s a moot point. For the record I still believe that both genders can be friends without either thinking of sleeping with the other.

As for the friend at the beginning of this post, she decided against it. Even though on paper it looked good, the reality for her was realizing that the feelings she had for him were strong, but not in that way. They are still best friends.



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