1. You need to know where you both stand before getting physical

Part of what ruined the experience for me was that I wasn’t sure what I was allowed to do and not allowed to do — outside of the bedroom. Did this mean I could date other girls? What if I kissed one of them? What if I slept with one of them? Outside of actually being in a relationship with someone else (i.e. Cheating on her with the FWB), what was OK?
I was always under the impression that a friend with benefits was supposed to be stress-free and rather casual. Our situation quickly — very quickly — began feeling more like a relationship than what I thought being friends with benefits should entail. Before you and your potential FWB get to it, just take the precautionary measure and know where you both stand.

2. I actually do hate the hook-up culture

I’ve always felt like that guy who was preaching against something he’s never experienced when talking down on the hook-up culture, but now that I’ve gone through it (albeit an awful one), I realized that it’s probably not for me.

I’m not judging those who like it (hey, to each his own), but I’m just not one of those people. I don’t like the, “So, what are we?” conversation, if one of you (or both) start feeling some type of way.

Plus, even if you have a FWB and you’re allowed to still casually date or see other people, it’s uncomfortable for me. I’m too busy to try and juggle two or more women in my life and, above all, I really don’t want to have to answer the question, “So, are you seeing someone else?” Even if you’re not doing anything wrong, it’s still awkward. “Well, I’m not like in a relationship with anyone, if that’s what you mean…” I clammed up just typing that.

3. I would take a relationship over any casual sex

I’m an extremely passionate person, in many aspects, but particularly physically. I like the feel of the woman I’m with, whether that’s casually holding her hand, massaging her head to toe, running my fingers through her hair, or cuddling with her.

You can’t do that with a FWB because touching is personal; cuddling is even more personal; and when things get personal, feelings form; and when feelings start to form with a FWB, it’s likely not going to result in anything good for either party.

Aside from physical passion, I enjoy talking to the person I’m with; learning about them; spending time with them — with clothes on. You know, things that shouldn’t even be thought of with a FWB. I can’t do the “Wham, bam, thank you, ma’am,” thing. It’s just too awkward. If you’re with a FWB, the sex will be more regular, but still, the “Get in, get off, get out” concept just makes me feel like an object, and that’s not a good feeling. If you sleep with someone randomly, I don’t like the awkwardness of debating with myself whether or not to call her after.

If I call, I’m afraid I’ll get the, “Um, it was a one-time thing; that’s it.” If I don’t, I’m even more afraid of being the guy who didn’t call. In a relationship, you don’t have that problem. The person is there — she’s always there, and you’re always there for her. There’s no awkwardness in that.

4. You need to actually know the person

I jumped into this situation with someone I barely knew, which is completely uncharacteristic of me. Admittedly, the proposal of a FWB situation intrigued me, but I still knew little, to nothing, about her.

I knew enough about her to know that she was fun to be around and that she was proactive enough to ask if I had been tested and whatnot. It may not be the sexiest thing in the world, but the biggest risk in sleeping with someone you don’t know is that you don’t know who they’ve been with or what they might have; the fact that she wanted to make sure we were both clean up-front was reassuring.

I’m not saying you need to know this person’s life story, and I get that the point of most FWB situations is that you really don’t get to know each other all that well, but you should know basics about them. Hell, I didn’t even know her last name until a couple of weeks in. Terrible.

5. People can’t handle the truth

Her stipulation was that, if I was with someone else, she would want to know so that she could stop with me. I was fine with that. I’m a man of my word and agreed. She said she would want to know beforehand, but if a situation occurred with someone else, I wasn’t about to stop mid-make-out and be like, “Hold on, I need to let my FWB know this is happening.”

I wanted to stop for a while, but, shamefully, I did like having the option there, especially when I had gone so long without sex for a while (see below). When something eventually did happen with someone else, I told her, but I didn’t go into detail (one, because I didn’t feel that she needed to hear, for her sake; two, it was really none of her business what happened, or with whom).

She accused me of “using her” for our time together, which let me know that my instincts were spot-on. She wanted to know if/when something happened; I told her (when, in reality, I didn’t need to say a word). If she couldn’t handle that, that’s on her.

6. Sex isn’t everything

Another thing I kind of knew before this situation, but was confirmed afterwards: Sex really isn’t everything. How do I know this? Because I had just ended a two-year dry spell shortly before diving into this and at times over that two-year span, I thought I would never have sex again. I had actually forgotten what sex felt like — that’s how long it was.

This situation put me in the position where literally all I had to do was show up and I would have sex. That’s it. After about a month or so, I found myself going there — “there” being about an hour out of the way from both my apartment and work — less and less often. I was essentially turning down sex. That’s when it was solidified to me that sex isn’t everything.

Yes, sex feels good; yes, climaxing during sex feels even better; but if there is no connection there whatsoever, it really kind of defeats the purpose of intimacy. Again, granted, a lot of people just want to view it as “banging” rather than “making love,” or whatever justification they want to give themselves, but I think that when you share your body with someone, there needs to be more there than just two naked bodies.