When your dating and hookups feel like a long line of really bad choices

People have sex for all kinds of reasons, and you could get something out of bad encounters that excites your subconscious even as it sabotages your conscious well-being. 

Q:

I think I may need an intervention. I have terrible taste in men for romance and sex. 

My ex is toxic, but I have gone back to him twice. One minute, I’m over dating, the next I’ve met someone I want to see seriously. One morning, I want to take a break from sex, that afternoon I’m saying goodbye to another online hookup.

I’m constantly turning over a new leaf on men, only to feel compelled in the moment like I simply must have sex with this person.

My current situation surrounds a closeted younger guy at work. He’s 23. I’m 37. One minute I’m thinking we should just be friends, next minute he presses his leg against mine and I think I might go for it. 

Dear One Minute Next Minute:

My head is spinning, so I can see why you are spiraling. You might need a deep dive into your self-esteem and your motivations around sex. People have sex for all kinds of reasons, and you could be getting something out of these encounters that excites your subconscious even as it sabotages your conscious well-being. 

Many people are simply drawn to drama. We become addicted to the adrenaline, then create situations for the thrill even though we know it’s ill-advised.

You already know that your ex is poison, and that the chase for tricks is more satisfying than the catch. Please reach for the inner strength and emotional support to stop making the same mistakes.

As for your 23-year-old colleague, it’s normal for him to test the waters with leg presses in the car, but it’s not normal for you to take advantage of it. It’s not fair to waffle on your feelings and take his still-closeted emotions along for the ride.

Q:

After the end of my 10-year relationship, I got reacquainted with myself as a solo act, and I became a Grindr power user. Now that I've had enough time with both, I'm open to dating again. But after a decade off the market, it's a whole new world out there. 

Back in the day, you didn't have to navigate the end of a fun date, only to then cross paths an hour later on Grindr. How do I get comfortable in this new dating reality? 

Dear Old Dog with Tricks:

The technology changed, but running into someone after a date, perhaps a bar, did happen when you were young, fun and slutty. Now that you’re fun and slutty but not as young, the awkwardness is the same, though maybe better since it’s not face-to-face.

You probably just forgot, but tricking pitfalls are many, and the “problem personalities” are plenty. Maybe it lost its luster after a real relationship, because the payoff doesn’t look as good as it used to — in either the pursuit or the prize.

The answer to returning to real dating is still the same as your glory days too. You’re most likely to meet your match while living your best life doing things you love — things you love besides tricking.

The Q is for entertainment purposes and not professional counseling. Send your burning Qs to [email protected].

Illustration by Brad Gibson

This column originally appeared in Q magazine. Read the latest issue, enjoy all of the past editions of The Q advice column, and look for a new issue of Q each week online and around town.