It's A Pleasure

I Haven't Had Sex In Three Years & Feel Like My Confidence Is Shot

Don't panic — this isn’t like trying to recall the three years of French you took in high school.

Originally Published: 
If it's been a while since you had sex, don't panic. You already know everything you need.
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It's A Pleasure

Q: You’re probably going to just respond with “Hey girl, up your therapy appointments and go smoke something!” but here goes. I haven’t had sex in about three years, and I’m just completely unsure about how to approach it now — even though I was very wild and extremely confident in my sex life (and sexual capabilities) in my early 20s.

Four years ago, I broke up with my longtime boyfriend when one of my parents got diagnosed with cancer. I moved out of our apartment and in with my parent and became a caretaker for them. Other than going to work, I put ALL of my energy into them for a year. They passed away at the beginning of the pandemic, almost immediately after my office transitioned into work from home and everything shut down. Dating wasn’t an option, and sex with a stranger during a pandemic was absolutely off the table.

Recently I’ve been flirting with a guy I went to school with, but every time we talk about hooking up, I immediately back out. The pandemic definitely created social anxiety for me, and there’s also some emotional anxiety after losing a parent that years of therapy and meds still haven’t quite fixed. I feel like I’m going to mentally psych myself out the entire time worrying about how I look, if I’m pleasing him, if I’m pleasing myself, and the emotional side effects.

But here’s what I’m stuck on: If not this guy I went to school with, then who? Online dating is an absolute horror show, there’s not a lot of single men where I live, and my new favorite place to spend my weekend is my sofa, and so far, zero men have randomly shown up in my living room ready to have sex with me.

A: Look, I’m never going to recommend against the heady combo that is therapy and smoking something. Far be it from me to instruct anyone to shun those two medically backed ways of tackling grief and anxiety. (There are many, many articles about weed helping people with grief!) That said, it’s actually not my suggestion or, at least, not my only one.

First (and perhaps hardest) thing’s first, you have got to give yourself a break. A major one. Think about what you’d say to a friend in your exact same situation. If I came to you and said, “I was a caregiver for a year for my parent, who had cancer, and then they died, and that was right at the beginning of a global pandemic that has lasted for years. Oh, and right before that, I broke up with someone I’d been with for the amount of time it takes to get a bachelor’s degree.” You would probably say something like, “Holy sh*t, that is a ton of impossibly hard things in a row and on top of each other; I can’t believe you’re standing up right now.” Either that or you would say, “‘Global pandemic’ is a little redundant.” But still, I know you’d have a whole heap of compassion in your heart toward my situation. And you’d probably even understand, somewhere in your mind, that I could not possibly be the same person I was before this series of events.

Grief is a multi-car accident. A pileup. Of course meds and therapy haven’t “fixed” this grief. Nothing will. It’s totally unacceptable, this amount of grief. Will medication and therapy change the grief or at least what you’re capable of handling? Yes. Will they “fix” anything? No. And I would argue gently that grief is not a thing to be fixed. Grief is of value. Not to be all WandaVision, but grief is love. You do not want medication that makes that go away.

On top of grieving your parent, which is a full endeavor of its own, you are also going to have to grieve the person you were before all of this “started.” The depressing, intolerable truth is that the person in their 20s who was having fun, wild, uninhibited sex is gone. The lovely twin truth of that, though, is that someone else with more depth and maturity and knowledge and life experience is standing in their place. And! Let me be so clear: This new person you are becoming is also very capable of having smoking hot sex. Fun, wild, uninhibited sex even! But first, you have to work (ugh) to accept that it’s not going to come in the same ways and on the same timeline it would come to 20-something you.

When it comes to sex, the amount of time since you’ve had it is practically irrelevant because each time (especially with a new person) is different. You haven’t forgotten any key pieces of information. This isn’t like trying to remember how to use the three years of French you took in high school to explain how you broke your leg in a discothèque. You have all the info you need. You know how to communicate with partners. You know at least some of the stuff you like or have liked in the past. You know that when something feels good, you keep doing it, and when something feels bad, you put a stop to it. That’s all sex is!

Now, that's not to be dismissive of how daunting it feels to jump back in, but I just want to remind you that you have handled more crap in the last four years than many people handle in decades. You are not ill-equipped for hard things.

If you know you want to hook up with this guy, you might try not giving yourself an out. Try to push through the awkwardness and discomfort of it all with 20 seconds of insane courage. (Yes, this is from We Bought a Zoo, but it’s still good advice.) If, however, you are not sure if you want to have sex (or sex-adjacent fun) with him, give yourself time. Consider also giving him a heads up so he doesn’t assume your hesitation is a lack of interest. It can be as simple as, “I’ve had a really hard couple years, and I’m kind of anxious about hooking up with someone right now, so that’s why I’m taking this so slowly. It’s not about you at all.”

When you do find yourself in the OMG-I’m-about-to-hook-up-with-this-person moment (and you will!), my sole piece of advice is to let go — much easier said than done, of course. But try not to think about your pleasure or his pleasure or how it’s going to end or what positions he prefers or if you look weird doing something. It’s sex; it’s meant to be fun! It’s the same as going bowling or playing Yahtzee or whatever activities people under 64 are doing. It’s a fun thing two people are doing together. That’s all. It’s not a measure of your worth. It’s not a compatibility test. It’s not a gift you give someone because they’ve flirted with you for X amount of time.

Also, so what if the sex you have the first time you’re back on the field is meh or awkward? Who cares! This isn’t indicative of all the sex you’re ever going to have. The importance of this first time having sex after a while is entirely built up by you, and you can dismantle that belief, too.

Finally — and let me briefly say this is the most common question I get now — I don’t know where you can meet people. I could tell you to get out and go to bars, and you could go to one every single night for 14 years and then end up falling for the guy AAA sends to fix your flat tire. Is going out “better” than staying in when it comes to meeting people? Sure. But I don’t think putting yourself in boring-to-you situations lends itself to finding heart-stopping romantic connections. Forcing yourself into things makes for a grumpy, miserable, and hopeless time at an ax-throwing bar — not true love.

My suggestion is to simply fill up your life with things that feel good. (And that includes sitting on the couch for a certain percentage of your time!!!) Just fill it up. The more good things, the better. Steal joy wherever you can. Try out new things, stretch your comfort a bit, but skip places and situations that don’t feel deeply rewarding or joyful.

There are already too many unpleasant things we have to suffer through in this life. If getting quasi-rejected via dating apps or slogging through a speed dating event isn’t your bag, skip it. Let life unfold; let yourself meet people while you’re doing things you actually like doing. There’s no rush.

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

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