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‘Will I Be Single Forever?’ and Other Pressing Questions

We’re excited to kick off the first installment of our new relationship advice column. Today, we’re answering two reader questions about dating (and we’d love to hear your takes, as well)…

Q. “Am I going to be single forever? I’m 30 and have been single for over three years. I’ve been on over 40 first dates since then and I’m feeling like it’s never ending.” — Louise

A. Louise, I feel you. I’ve been you. And judging from many other reader comments, a lot of people are in the same boat at this very moment. Dating can be hard. And sometimes, it can feel endless.

First off, know that you are not alone. I spent years going on countless first dates. Dates who mansplained my own job to me. Dates who insulted the way my toes looked in sandals. Dates I thought I sparked with, who promptly ghosted. Dates who were perfectly lovely people, but there was no connection. And on and on.

Coupled friends would say things like, ‘It’ll happen when you least expect it!’ and I would want to throw my fries at them. Eventually, (because I had no other choice) I leaned the eff into my single-ness. I focused on the nice things about it — taking up the whole bed; having full command of the remote; decorating however I wanted; enjoying time and space to myself. By my mid-thirties, I completely gave up on finding a partner and really enjoyed the shape of my life. And then I met someone.

Here’s another anecdote. I have a friend, we’ll call her Snuffleupagus (definitely not her name). Snuffleupagus is the quirkiest human being you could ever hope to meet. I say this with love, because her quirks are part of what make her amazing. But she herself would admit it takes a very special, equally quirky, person to be a good match. To make matters more complicated, when it comes to dating, she is the pickiest person in the entire universe. Every potential partner failed to meet her very long, very specific list of standards. ‘Try to keep an open mind!’ everyone said, to no avail, as we watched her reject date after date.

Well, it certainly didn’t happen overnight, but one day, Snuffleupagus met the person of her dreams. What’s more, they recently got engaged. If Snuffleupagus is happily coupled, I promise, there is hope for us all.

But you asked if you would be single forever, and it’s my job to give you an answer. Because I am not an oracle, let’s turn to math. This video calculates the equation of finding your soulmate(s). (Hint: the odds are pretty good.) The overwhelming majority of humans will find a mate — if they so choose. Remember, it only takes one.

In the meantime, though, focus on what matters — you. Try to appreciate how each date with Not The One gets you closer to understanding what it is you want and need from a partner, as well as what you want and need from yourself. Collect funny stories for one day when you aren’t dating anymore. And know that when you do find someone, all these dates will make you all the more ready for the good things in your future. — Caroline

Q. “I am 25, and I feel insecure about my lack of experience, especially with the physical side. I’ve only ever kissed two people and never had sex. I feel like I’m too old to be this inexperienced. How do I move forward with these feelings of insecurity?” — Jess

A. First and foremost, please know you are in great company! There are so many people who have non-traditional dating timelines. (Also, what even is non-traditional?) I remember in my senior year of college, half my sorority was engaged and I hadn’t even gone on a date. I was also terrified that I would never figure out how to have good sex.

After going through my twenties never dating, last summer (at age 30) I decided to face my dating fears head on and just date as many people as I wanted, no expectations. I was nervous at first, but after a while it was so much fun and empowering. I realized that none of my dates knew about my various insecurities or lack of experience — I could be as confident as I wanted to be with each new person!

Lack of sexual experience is a common fear, but I found that a lot of the physical aspects come pretty naturally; the less you’re in your head and the more you let yourself be in the moment with that person, the better it will be. I used to think that everyone who was dating had so much more insight than I did, and that’s also not necessarily true. The more you become comfortable with yourself, the more you’ll realize there’s nothing to be afraid of.

I’d also encourage you to cultivate a sexual relationship with yourself, if you haven’t already. It’s said the most important relationship is the one you create with yourself, and I believe the same is true in the sexual realm. Understanding your body — what you like and don’t like, where you like to be touched — will not only help the other person, but will also help you become more confident when you decide to be physical with someone. 

So, while you’re not dating, think of the kind of person you want to be with and how you want to feel with them. Explore different ways to know yourself more — take yourself on dates with coffee or a cocktail, on a long walk around your neighborhood, make your favorite dinner, watch a beloved movie. When you do feel comfortable to begin dating, don’t be afraid to take the reins and step into your confidence. This is your dating life, and it can be whatever you want it to be. — Kim