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Treat your hookups like people you might actually see again and you might actually see them again

Is it possible for a hookup to turn into a relationship?

Hoping One Person Enters

A hookup is a relationship, HOPE. It may be a short-term relationship, but it's a relationship regardless.

And, yes, a hookup can turn into a long-term relationship, but not if you're treating your hookups like shit (because they're only hookups!) and not if you're willing to let the people you hook up with treat you like shit (because you're only a hookup). Treat your hookups like people you might actually see again and you might actually see them again.

Sometimes people hook up with strangers precisely because they wanna have sex with someone they don't expect to see again. That's not always a bad idea. A girl who can't let herself go with a guy she's dating — maybe she fears being slut- or nympho-shamed by a boyfriend — will grind the dick off a hookup. And it can be easier to ask someone you don't expect to see again to do something kinky. Say a straight boy has always wanted a girl to put him in her panties and peg his ass. He could ask a girlfriend to do that, but the stakes are higher. What if she freaks out and dumps him, and blabs to her friends?

People who divide the fuckable world into those they care about (and can't open up to sexually) and those they don't care about (and can open up to sexually) wind up having awesome sex with people they don't know, and lousy sex with people they marry. That's not a good strategy for a successful long-term relationship.

So be uninhibited with your hookups while treating them like people you might actually see again, and insist on being treated that way in return.

Finally, some people treat hookups like shit — only after they've come, natch — because they're not interested in a relationship. That's not just assholery, it's completely unnecessary assholery. If someone was kind enough to fuck your brains out, a little kindness and consideration isn't too much to ask. If you're worried your hookup might misinterpret "kindness and consideration" as "I want to be with you forever," tell them — gently and directly — that you're not interested in a relationship.

Straight guy here. For the first time, I am with someone who understands how much my work is a part of who I am. (I travel for research and come home and agonize over writing it up.) We have a caring and affectionate relationship. She told me at the start that she has never had an orgasm and she didn't believe in masturbation. I knew the sex would be vanilla, but I didn't realize that a year later, it would be more vanilla and less frequent. I'm going out of my mind. In the early months, we discussed open relationships. Her view was that she wasn't interested, but if I cheated it would be fine as long as she never found out. At the time, it sounded like a trap; now it sounds like an option. Help.

Sex Too Underwhelming Can't Kontinue


Since an honest open relationship is off the table, STUCK, I'm gonna urge you to DTMFA. (I'm not saying your girlfriend is an MF, but DTMFA is the term of art around here.) I'm thinking you'll have an easier time getting a girl who likes sex to understand how important your work is to you than you'll have getting this girl to understand how important sex is to you.

I am a girl and I am stuck. My boyfriend and I have been dating for nine months, and I only recently told him I can squirt. When we had sex before, I would tell him to stop before I came because I didn't want to squirt. Now he thinks it's really hot and wants me to do it. But I can't seem to get to that point anymore. When I masturbate, I can squirt no problem. But even with me, or him, stimulating my clit while having sex, I can't do it.

What Should I Do?

You should relax.

I'm not saying you'll squirt the next time you fuck, but you'll get there sooner if you relax about whether or not you're squirting.

You weren't squirting with the boyfriend because you worried that he might react negatively. Not squirting was something you were doing for him. Now that you know he's into it, you want to squirt for him.

Stop thinking about him, and start thinking about yourself.

You trained your body not to come when you were with your boyfriend, and it's going to take time to undo that training. But if you can squirt when you masturbate alone, you can squirt with your boyfriend. Here's how you can get there: Masturbate with your boyfriend in the house but not in your room. Then do it with him in the room but not in bed with you — put a blindfold on him if you're self-conscious about him watching. Then masturbate with him in the bed with you blindfolded. Then masturbate with him in the bed with you not blindfolded. Then masturbate with him in the bed and not blindfolded and touching you, then with him in the bed holding you, then with him in the bed helping you.

Relax, enjoy, have fun, and you'll get there, I promise.

The advice you gave to TUSH — the gay teen-ager worried he and his boyfriend weren't good at gay sex — isn't exclusive to the gay young'uns. Most of us don't start with the practice and communication often required for successful sex. My first attempts, as a virgin male with a virgin female, were hilariously awkward. Fifteen years later, with a combined 30 years of experience, we hooked up again for one of our best-ever sexual encounters. Like anything worthwhile, it takes time and effort and practice.

Only Learning Doth Make A Notch

Thanks for sharing, OLDMAN.

Find the Savage Lovecast (my weekly podcast) every Tuesday at thestranger.com/savage.

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