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Help! I’m 25 and Have Never Been Kissed

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Dear Randa,

I’ve got a not-so-dirty little secret: I’m 25 and have never been kissed. After some good ol’ therapy, I’m over a lot of my trust and intimacy issues, and I’m ready to make up for lost time and pucker up. The problem is I don’t know how to get started; I’m a great wingwoman, but I’ve never stepped into the arena myself. Plus, how do I tell someone I’ve never been kissed without it being a big thing? Do I tell them?


Perpetual Wingwoman

Dear Perpetual Wingwoman,

While your predicament might feel unique, you’re not alone in feeling confused about what to do with your dating life. I can tell you from experience that the social norms of dating, including first kisses, are more nebulous and uncertain than ever.

You seem to have accepted where you’re at, but you’re concerned about how your lack of kissing experience may be a “big thing” to other people. I think you’re right to believe that you’ll be perceived differently if you tell someone you haven’t been kissed at 25 (the average age of a first kiss is 15), but just because you’re an outlier doesn’t mean you’re totally doomed.

My friend, whom I’ll call Jo, self-identifies as a late bloomer. She blames her lack of experience on her strict Asian immigrant parents and got on dating apps only when she graduated from college and left their clutches.

Jo’s approach to her first kiss may feel relatable: “I kind of brute-forced it, like, Okay, it’s time to grow the fuck up. You’re a type A person. It’s time to just put yourself on a fucking deadline. I was so ashamed because I was 22. Like, This should have happened by now.” She was worried that telling someone she had never been kissed would make her “look weak and embarrassed and less attractive.” Admitting to being a late bloomer may bring up some questions, but if someone drops you for it, they’re probably a big meanie and not worth your time.

Anyway, Jo ended up going on a few dates with an “archetypal Stanford engineer,” and she didn’t tell him anything about her lack of experience. One day, when she was about to get out of his Mini Cooper, he kissed her: “I just kind of froze. It was a very dry, awkward kiss. Not the most sensual or romantic.”

I think the expectation of “sensual” or “romantic” first kisses is kinda unrealistic, regardless of age, and if you have that expectation, it’s probably worth letting it go. Maybe yours will be out of a movie, but when I texted a bunch of friends to ask about their first kisses, their experiences basically fell into one of two categories: awkward or drunk. My friend Claire said it felt like she was “kissing a frog” — and not in the fairy-princess way: “It was slimy, and the act of it felt kind of reptilian.” Katie, who identifies as a very anxious person, got her first kiss at 20. She was simply excited “that he didn’t stop midway through and say, ‘Is this your first kiss? You’re really bad.’”

Any anxious person can probably relate to this; it can be scary to look like you don’t know what you’re doing. But I think Katie’s experience is pretty universal. No one is going to stop you mid-kiss to tell you it’s bad.

Lest you dismiss Katie and Jo’s first kisses as still young enough to be “normal,” I found a guy who crossed the kissing chasm at 27. Derek explained that the delay was due to low self-esteem born from cystic acne and postgrad unemployment. “I convinced myself that it wasn’t even possible,” he said of his first kiss. “I was stuck in a loop of negative self-talk.”

Just as you’ve worked on your intimacy issues, Perpetual Wingwoman, Derek focused on his self-esteem: He got on Accutane, joined the Air Force, and went through a “slow, gradual process of improving my confidence.” Eventually, he worked up the courage to go on some dating-app dates. One in particular was going really well: “We were just really engaged, really talking. I was talking so much that my mouth was drying out. So, good nervous energy there.”

He invited his date over to his place, and she accepted. Relying on the countless advice posts he had read over the years, he broke the “touch barrier” and moved in closer as they were flipping through some of his books, and when the timing felt right, he just went for it. Reflecting on the experience two years later, he said, “It was better than having sex for the first time, I’d say. I rode that high for about a week.”

Derek’s experience illustrates clichéd advice we already know: Confidence is everything. When you’re not so caught up in how the other person might think you’re a loser, you’ll connect more easily and intimacy will happen more naturally.

So now that you know what to expect from a first kiss, how do you even find yourself in a kissing situation in the first place? Derek lays out a pretty good playbook. Meet somebody either on an app or IRL. Hang out with them one-on-one. Make eye contact. Touch arms. Smile at them. Is it completely insane that I’m laying this out step-by-step? Maybe. But you asked the question, and I wanna make sure we cover all of the intricacies involved in the act known as first base.

As for where you may do it, I polled the Hot Singles Instagram following. People suggested locations such as a bridge, a rooftop, or sitting on the same side of a booth at a bar. Harry, 27, felt strongly about the sidewalk: “You can’t kiss on the sidewalk unless you’re a teenager.” But, he added, “You’re allowed to do whatever you want when you’re in love.”

And lastly, let’s talk about whether or not you should tell the person it’s your first kiss. Most of the people I spoke to stayed mum, which makes sense. I mean, let’s say you’re in the thick of it — heavy arm-touching, making prolonged eye contact — and the kiss is about to happen. The person is leaning in — are you going to stop them to say, “Wait! I’ve never been kissed”?

You could, but I think you should tell them after you’ve kissed, if you feel like it. They won’t be able to tell it’s your first kiss, and you don’t owe them that information.

Ultimately, I think a lot of your anxiety has to do with our unrealistic expectations that everyone will and should have been kissed by a certain age. I found plenty of people who haven’t been kissed for good reasons, but everyone I spoke to about it felt ashamed. Jo told me she resented being “prude-shamed” by her more “sexually liberated” friends in college. In hindsight, the whole female-empowerment narrative around hookup culture was never right for her: “I wish someone would have been like, ‘There’s actually nothing wrong with you; you might just be a demisexual person who needs meaning and emotional attachment to someone before physical intimacy, and that’s actually a really beautiful thing.’”

I agree with Jo: There’s nothing wrong with you, but you are different from most people. That gives your story a lot more texture and intrigue than everybody else who kissed their middle-school crush under the bleachers or whatever. We’ve heard enough of that. Good luck out there!

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Help! I’m 25 and Have Never Been Kissed