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‘I’m in My 30s and Have No Dating Experience!’

Dear Sara: I’m 32-years-old and have zero dating experience—like, I’ve been on three first dates. I’m not ugly. I’m actually quite pretty. I am plus-size but not morbidly obese, so it’s not like I haven’t been asked out. I have been. Not a lot mind you. But it’s happened.

The truth is, in my twenties I struggled with mental illness–horrible depression, anxiety, and panic attacks. That made dating nearly impossible. I was so insecure. I was afraid of men and of having to speak to them. So now that I’ve gotten help for my mental illness, I’m ready to get out there. But I have no idea what I’m doing. I’ve never had male friends. I could barely speak to the guys I worked with or went to school with. On top of all of that–and this is SO embarrassing—I’ve never even been kissed. Obviously, I’m a virgin. I never intended to stay one. I feel like there is something wrong with me. What guy isn’t going to think I’m strange? I’m a successful woman. I have a great job, as well as friends and family who love me and think I’m great. I’m just totally and completely clueless when it comes to dating and men. How will I get past this part of the conversation during a date? How will a man deal with my lack of experience?  — V

Dear V: Let’s start with the good news. You have work you love and terrific relationships with your friends and family. So whatever issues you’ve dealt with in your past, you’ve clearly managed to overcome them in nearly every area of your life. So why would you think dating would be any different?

My guess is it’s because everything in our culture tells you it is. For some insane reason, our society gives more respect to the person who burns through a series of disastrous relationships than the one who waits until she’s ready, or until she meets the right person. Even worse, much of our dating culture conditions people to view themselves as commodities, whose value depends on some abstract idea of supply and demand. You’re supposed to present yourself as someone whom lots of other people want—someone who is only single because she has refused so many other offers. Lots of people get stuck in this trap.

But if you’re simply looking to find a nice person to share your life with, then there is no reason to worry about pleasing the majority. You don’t have to fashion yourself into some cultural ideal. You don’t need to prove that you’re better than anyone else. You just need to find one person who loves you the way your friends and family do—and whom you can love back in the same way. Neither of you has to be perfect, or even close. Neither of you has to meet any external measures “normalness”—you can both be weird, if you like, and love each other for it.

Instead of seeing your lack of dating experience as a black mark, I’d suggest you look at it the other way. You had some troubles, and now you have them under control. A great many people suffer from anxiety and depression, as the popularity of prescription medication can attest. So you’re not an outlier in that you’ve had some mental-health issues; you’re an outlier in that you dealt with them before inflicting them on another person. So give yourself credit for that.

I understand that the idea of telling someone about your past on a first or second date seems intimidating. In his book, Love Illuminated, Daniel Jones, the editor of New York Times “Modern Love” column, says many daters feel anxious about revealing some unsettling fact about their life or past—an artificial limb, a stint in rehab—to the people they date.

I understand that this is daunting, so it may help to remind yourself that a date is not a job interview. You don’t have to disclose your entire history on that first coffee meet-up, or even the third dinner. You’re allowed to keep this information private until you feel comfortable sharing it.

If the two of you become serious, then of course you will need to tell them about your past. But rather than worrying about how and when to divulge this, I suggest first focusing your attention on how and when they have earned your trust.



its not you sara eckel

Sara Eckel is a personal coach and the author of It’s Not You: 27 (Wrong) Reasons You’re Single. You can get a free bonus chapter of her book at You can also find her on Twitter and Facebook. Ask her questions here.