Why Most Friends With Benefits Relationships Don't Work







This Tik Tok got me thinking about Friends With Benefits Arrangements and why they typically don’t work. We talk more about this in this week’s Substack podcast.


Let’s first unpack the term itself.


Friends = Someone with whom you share a mutual fondness and regard

With = Implies that friend comes to the table accompanied by something

Benefits = Physical intimacy


The mistake I see many people make is they enter into these casual entanglements with people with whom they were never actually friends. They decide to be FWBs with people they met online or briefly dated. They didn’t take the time to establish a solid foundation of friendship before agreeing to the FWB arrangement.


Eventually, one of you is going to start dating someone and end the FWB relationship. That decision will make the other person acutely aware of the fact their FWB partner would sleep with them but not date them. I think the “friends” label makes the arrangement feel less transactional. It’s a way to justify hooking-up with someone you know does not see you as relationship material without feeling bad about it.


The topic of Friends With Benefits reminds me of a recent Tik Tok I posted suggesting that men not be too direct about just wanting a hook-up. Approaching it from that angle is dehumanizing as it first and foremost makes the woman uncomfortable. The better way is for the man to ask a woman out for a drink then just ask her back to his place. If she’s open to a casual hook-up, she’ll go. If she’s not, she won’t. (Obviously, if he’s asked what he’s looking for he shouldn’t lie but rather circumvent the question with a vague response like wanting to meet new people and see where things go.)


What a lot of men do is take a woman out a few times, give her a taste of what being in a relationship with him would look like, then drop the hammer. They’re not ready for a relationship but would love to keep hanging out. You know. Casually. Often times the woman is already attached so she agrees. Meanwhile, he’s out there dating other women looking for a long-term relationship knowing he has consistent sex just a text away.


In the Tik Tok I linked above, I think what bothered that woman most was that her FWB disappeared for a window of time - presumably while he dated someone else - then reappeared and wanted to hook-up. I’m not sure it was the request of a Golden Shower that irritated her so much as the possibility he’d been dating someone else. That’s not to imply she had feelings for him or wanted more. I believe her when she said he didn’t. What I think upset her was the way he handled his reappearance. Instead of showing interest in her life and catching up, he jumped right to the sexual request, making it very clear he only saw her as a sex partner. He didn’t see her as a human being. By coming at it that way he dehumanized her. He also made it abundantly clear that she was in the sex-only zone. Even if that’s what she is, nobody wants or deserves to have that fact thrust in their face in such a thoughtless manner.


All this is to say while I don’t recommend these sorts of relationships, I think in some rare cases an FWB agreement can work. However, in my opinion, two criteria must be met.

  1. You have to be FWB with someone you know - unequivocally - is not relationship material.

  2. You need to have very clear and expressed boundaries.

A successful FWB requires finesse from both parties. We navigate the FWB waters by remaining in a state of denial. We both know we’re a pit stop of sorts.


We just don’t want to know. You know?

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