Dear Dan:
Is it possible for a hookup to turn into a relationship?
Hoping One Person Enters
A hookup is a relationship, HOPE. And yes, a short-term hookup can turn into a long-term relationship, but not if you're treating your hookups like shit or you're willing to let the people you hook up with treat you like shit. Treat your hookups like people you might actually see again — like human beings with human feelings — and you might actually see them again. You might even wind up in a long-term relationship.
Now, sometimes people hook up with strangers precisely because they wanna have sex with someone they don't know and don't expect to see again. And that's not always a bad idea: Having sex with someone who you don't expect to see again can be very liberating. A girl who can't let herself go with a guy she's dating — maybe she fears being slut- or nympho-shamed — 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.
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 but won't date) 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 anyone interested in a successful long-term relationship.
So here's what you should do, HOPE: Be uninhibited with your hookups while treating them like people you might actually see again, and insist on being treated that way in return.
Dear Dan:
Straight guy here. For the first time in my life, I am with someone who understands how much my work is a part of who I am. 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 then that 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 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, I'm gonna urge you to DTMFA. (I'm not saying your girlfriend is an MF — heavens no — 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.
Dear Dan:
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 would have sex before, I would tell him to stop before I came because I didn't want to squirt. Now that he knows, he thinks it's really hot that I can and wants me to do it. But I can't seem to get to that point anymore. I have a vibrator, and when I masturbate, I can squirt no problem. But even with me or him stimulating my clit while having sex, I just can't do it and I don't know why.
What Should I Do?
You should relax. I'm not saying that you'll squirt the next time you fuck your boyfriend if you can just relax, but you'll get there sooner if you relax about whether or not you're squirting.
And let's remember why you weren't squirting with the boyfriend: You were worried that he might react negatively or think it was gross. 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.
Dear Dan:
The advice you gave to TUSH — the gay teenager worried because he and his boyfriend weren't any good at gay sex — isn't exclusive to the gay young'uns. Most of us don't start with the discipline of practice and communication often required for mutually successful sex. My first attempts, as a virgin male with a virgin female, were hilariously awkward. Nothing worked, nothing fit. Fifteen years later, with a combined 30 years of experience, we hooked up again for one of our best-ever sexual encounters. Please let the gay kids know they're not at all alone in this crazy game of sex.
Only Learning Doth Make a Notch
Thanks for sharing, OLDMAN.
