It's A Pleasure

I Want To Start Dating Again But I'm In A Funk. How Can I Get Out Of It?

It’s all about baby steps.

How to get out of a funk and start dating again.
Ivan Ozerov/Stocksy

Q: I haven’t had sex in five to six years due to some depression and body image issues followed by a literal pandemic. I want to start meeting people again and have plenty of options on the apps (I pay to see who has already liked me), but I am experiencing a serious mental block. Any advice on how to get out of it?

A: Not to be Peter Kavinsky, but whoa, whoa, whoa! I think you have innocently gotten ahead of yourself. I’m not, to be clear, suggesting that I don’t think you’re ready to get back on Ginuwine’s proverbial pony. You absolutely have everything you need inside of you already to get there — this feels like the climbing the pole scene from Mulan, sorry. I think you have a mental block because you’re imagining a lot of stuff that you frankly aren’t even faced with.

You’re trying to get your brain ready for deep-sea scuba diving when you’ve been invited to a rooftop pool party. To overextend this pool party metaphor a bit, yes, pool parties can suck and be uncomfortable or embarrassing, especially if they take place in seventh grade, but they are meant to be a fun chill time. What you have in front of you, namely sex, is supposed to be a fun, chill time. I want you to think long and hard about the fact that sex is meant to be fun. Is it automatically a grand old time with every single new partner? No. It takes a little bit of pushing through awkward moments, talking to people you realize you don’t actually like, and forcing yourself to relax (kind of like a pool party).

You’re freaking out about step 128 when you haven’t gotten past step 47! Every single thing that happens romantically for you will take a lot of buildup. Sex isn’t one thing; it’s a bunch of little moments strung together like a Christmas tree popcorn garland. You don’t just have sex with someone; you meet someone at an Autozone, you start flirting with them, you realize you’re both from Montana, you exchange numbers, you stalk each other on IG, you agree to overlook that they like EDM, you agree to a coffee date that turns into a walk to a bookstore that turns into getting a drink that turns into dinner that turns into “come back to my place” that turns into “I can’t because my car is at Autozone” that turns into a semi-obscene Uber ride that lowers your rating on the app. Or something like that. Sex is the culmination of a whole lot of moments and decisions that you have control over. There are exit ramps galore! Despite what bad early 2000s porn might suggest, it’s pretty difficult to stumble your way into having sex with someone.

My advice is this: baby steps. Do this sh*t in the order it comes up! You have no idea what you might have with someone. This is not a car dealership where you’re being offered a bunch of options and upgrades and you simply have to decide which fits your lifestyle. This is about meeting real, actual people and feeling out what works and what doesn’t. Nothing is predetermined with anyone. There isn’t one type of sex a person has and can “give” you — you two create intimacy together. And I don’t exclusively mean in Very Serious Relationships. This is true for casual hookups, too. You decide what is and isn’t on the table and when, and it might change in the moment. You might feel like Tonight’s The Night!!! and it turns out that you get a little too drunk and eat a pulled pork sandwich at the bar (mistake) and feel kind of ill and now you just want to go home. Or you might make what feels like an impulsive decision that ends up working out totally for you.

You don’t know what’s going to happen because you haven’t started anything yet. There’s nothing you can imagine that will be close to what getting back out there is actually like because you’re going to be meeting real, nuanced, unpredictable people.

So take it slowly. Go out to a place that feels comfortable, talk to one person a week on the app and see how it feels, flirt with someone in a low-key way. These baby steps will start to stack up on top of each other. Try your best to ignore the big picture outcome (harder than it seems!) because the truth of life — despite our very strong human urge to assign narrative to a bunch of interlocking events — is that there really isn’t a single, fixed outcome. It’s not like things just reach a clear endpoint one day where the future is settled. Even rituals that seem to connote the settling of things — like graduations marking the end of school — are not final; they’re the beginning of something else. New moments, new memories, new futures. Try your hardest to stay in the moment. That doesn’t mean that you ignore red flags for the future or that you have no idea what you’re looking for in a partner. Just try to remind yourself that catastrophic or alternatively perfectly euphoric imaginings of what might happen really aren’t your business. Your business is to show up, ask for what you want, be kind, and have fun. Stick around people who make you feel good, leave situations you dread, and be open to the fact that you have no idea where this is all going to lead.

In the meantime, I strongly suggest that you either seek out or continue to go to a therapist who you can talk to about the specifics of what you fear, what you want, and what you need. A therapist would be a great person to talk about issues around depression and body image, which can very easily crop up again when you start dating. You’re more than ready for this, but the more help and support you get along the way, the better. Again, the goal is to have fun — dating is not an assigned task; finding someone to love, like, or hook up with is not homework — so make having fun as easy as possible!

It’s A Pleasure appears here every Thursday. If you have a sex, dating, or relationship question, email Sophia at or fill out this form.