Dear Dana: I’ve Never Been In A Relationship. Is It Too Late For Me?

Dear Dana is a bi-weekly advice column for humans who engage in romantic relationships. Please send your dilemmas, issues, conundrums, assumptions, conflicts, anxieties, worriments, obstacles, complications, predicaments, queries, questions, and any other synonyms for “problems” to

Dear Dana,

I’m nearly 25 and have never been in a romantic relationship, never had sex, and most of the time I have no desire to be involved with anyone. Every once in a while I get a crush and then spend so much time psyching myself up to talk to them the feeling passes, or it’s too late. I realize I’m not exactly proactive about finding a partner—I am rubbish at small talk and I am awkward in social situations. I also have horrible self-confidence, because of poor body image and being bullied throughout middle- and parts of high school. I cannot imagine having sex with anybody and the idea of it makes me incredibly anxious.

So no romance, and mostly no desire for romance, except every once in a while I get so lonely, and the longing is just too much, and being around couples is lovely, but also painful, and I’m throwing myself into hobbies and volunteering until I’m too tired to want anything. I’m doing the therapy. I’m doing the exercises. I’m trying so hard at the “love thyself” philosophy that everyone seems to recommend.

I’ve never been in a situation where romantic interest was reciprocated and I’m starting to think that it’s just the sort of person I am. (Can you tell I’ve been researching? Oh, I love to research.) But then, my thinking goes, if I was a gray-sexual/gray-romantic, why would I feel so much longing, or jealousy, or sadness when thinking about couples and my own past failings at relationships?

If I hear one more person tell me how I need to get a man/I’ll be married with children by the time I’m 25/it’s time for me to loosen up/bring down my standards/BELIEVE IN MYSELF I will bludgeon someone to death with my copy of Wild. I guess I’m asking how I might deal with my feelings head-on? Numbing doesn’t work. Distraction doesn’t work. Advice from family and friends doesn’t work. Medical advice sure doesn’t work. How the hell do I cope?

Thank you,



Dear Gray,

Fuck those bullies. Fuck that teasing. Fuck anyone who ever made you feel that your body wasn’t 100% fucking perfect. Your body is perfect because it lets you write and think and breathe and walk down the street and long for something you aren’t even sure that you deserve. Because your body is wonderful and it knows that you do deserve it. You deserve love.

For real: Fuck those bullies. Anything they said was about them and their pain and their inability to live with their pain without vomiting it onto someone else.

You have to understand that it is not at all weird to be 25 and to never have had a boyfriend. It feels weird, mostly because media tells us that everyone falls desperately in love with the neighborhood bad boy or a sparkle vampire or One Direction the second they reach sexual maturity. But the less-likely-to-sell-shampoo truth is that most people aren’t ready to fall in love until well after they’ve left high school. You may just now be ready, which is also why you’re completely freaking out.

You have told yourself that you are meant to be alone and that you will never have a romantic relationship. You’re writing to me as though you’re 75 years old and genuinely asking if pursuing a romantic partner is a waste of time. And if you were 75 years old I would tell you that there’s plenty of time to still find love, that everyone deserves to be happy, and that you can totally find a terrific partner. And I’m going to say the same thing to you, but this time with an extra: You are only 25 years old. 25! That’s one of the youngest ages out there! There’s no way you’ve wasted time or a ship has sailed—no one can see the water, your harbor is so full of ships.

I went through a horrible jealous period in my life. I was working full time, I had a boyfriend, my apartment had skylights in it, I had a group of friends I went out to fun comedy and improv shows with every weekend. Things appeared to be going well. But they weren’t. Because every weekend I sat in a theater, and the lights went down, and someone got on stage and started performing and my insides began to twist. I felt as though my stomach was trying to leave my body through my throat. The shows were good, the comedians and actors were good at their jobs—they were doing very, very well and being very honest and open and vulnerable and entertaining. And I hated their performances because I wasn’t the one performing. I was desperate to perform but I had convinced myself that I couldn’t. I told myself that I wasn’t talented enough to perform in Chicago, that I didn’t have the time or money for the training necessary to become a good performer, that it was silly to want to perform because I would never make money doing it, that I really should just be happy to go and sit the audience and watch others.

But I was fucking miserable watching others perform.

When you feel that pang of longing, that sick twist of jealousy, it’s how you know what you really want. You want to be in a relationship. You want to have romantic love.

The bullshit romantic advice that you hate isn’t wrong: Loving yourself is key. Because you have to believe that you’re worth someone else’s effort. Not to get them to like you, but to get yourself to open up enough that the other person has a chance of liking you. In order to find a partner you have to be vulnerable. You have to be willing to sit with the knowledge that you will be revealing yourself, and that you may be hurt. But you also have to know, absolutely, right down to the root of your big toe, that if you are hurt you will also be absolutely fine.

Do not assume that those who didn’t respond to your earlier tentative flirting and small talk attempts were rejecting you. Based on the tone of your letter, and the few glimpses you provided into your thought process, my guess is that your expression of interest in them was so finely tuned, so carefully measured, that the object of your affection never knew that you liked them. The world can’t hear your heart, most people are barely paying attention, and, when it comes to flirting, blistering clarity is usually best. “I like talking to you. Want to get coffee sometime?” is so clear, so unambiguous, and so fucking effective. Because you either get coffee or you don’t, and in either case your heart keeps beating. I promise.

So what did I do about my performance jealousy? For a while: nothing. I went about my life hoping that an improv troupe would overhear something funny I said in a coffee shop and ask me to join them. That plan was, of course, insane, and did not work at all. I grew more and more miserable until I finally had enough of my own misery and I signed up for improv classes. I spent $325 to stand in a room every Saturday morning and pretend to toss a fake fall back and forth with a group of strangers. And I felt like an asshole doing it and almost didn’t come back many times, but then I had paid my money so I kept coming back and tried to get more comfortable being uncomfortable. And taking that class and forcing myself to throw that fake ball around directly led to my current career as a performer. I’ve done hundreds of shows and I am giddy to report that I will do hundreds more.

I do recommend improv classes, though. I know you don’t want to be on stage, but you do want to be able to open your mouth and talk to someone without your brain beating the shit out of you the entire time. You can’t open up if your brain is yelling at you to shut up, or trying to game the conversation. You have to actually allow yourself the room in which to mess up, say the wrong thing, not be perfect. And then you’ll be human, and humans are kind of sexy.

Here’s how you deal with your feelings head-on: The next time you like someone, ask them out. I don’t care if you have to throw up 12 times before you do it, DO IT. Open your mouth, ask them to go out with you, and do not be surprised when no one dies. If they say no, then that is disappointing but everyone will still be alive. If they say yes, then you can anticipate a few more days of nervous barfing, but you will also have a date. Either way, you will have surprised yourself. You will have taken a step toward what you want.

All of the self-help maxims that make you cringe do so because they are not fully honest. They dance around brutal truth, but I do not. You have to go out and get what you want. You want it, you deserve it, but you aren’t owed it. No one’s going to show up at your house and give it to you. You have to resolve that the pain of not having what you want is worse than the pain of pursuing it. And it is. So go get it.

Dana Norris once went on 71 internet dates, many of which you may read about here. She is the founder of Story Club and editor-in-chief of Story Club Magazine. She has been featured in McSweeney’s, Role Reboot, The Rumpus, and Tampa Review and she teaches at StoryStudio Chicago. You may find her on Twitter at @dananorris.

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