I’m 38, and I’ve Never Been Kissed. Where Do I Even Begin?

On How To!, a professional matchmaker helps a woman find love.

Man and woman about to kiss
Photo illustration by Slate. Photo by Image Source/Getty Images Plus.

On a recent episode of How To!, Sharon came to us looking for love—more specifically, her first kiss. At 38 years old, Sharon has never kissed anyone or been in a serious relationship, but she’s determined to change that. In this episode of How To!, professional matchmaker Lisa Clampitt gives Sharon some tough love and shares tips on finding romance at any age or level of experience. This transcript has been edited and condensed for clarity.

Sharon: So I’m 38. I’ve never had a boyfriend, but I would very much love to be married.

Charles: I think it’s safe to say, based on what you’ve told me, that you haven’t had sex with a man?

Sharon: That’s correct.

I don’t trust myself when it comes to dating, so I’m almost always the one that cuts things off. So, I’ll go on a date. I don’t really feel any connection. And so I don’t really want to go on a second date.

Charles: That’s surprising to me that you’re the one who’s cutting this off. Why not just say, hey, I wasn’t in love at first sight, but why not just go on a second date?

Sharon: I’m trying to remember the last time I had a date. I think it’s been four years. I’m trying to remember when it happened. Gosh.

Lisa: But I think the fact that you’re saying it’s four years—No. 1, that’s an issue. You’re saying that you want to run a marathon and you’re still in bed. So I would say that’s your biggest issue.

Charles: Let’s say Sharon goes on this date, and she likes the guy. He’s nice, but she knows that she’s not going to end up marrying him. Should she go on a second date anyways?

Lisa: I don’t think that you can know who you’re going to end up marrying from a first date, if there are no deal-breakers. So I would say yes, because she doesn’t know. She doesn’t have that experience to be able to make that decision.

Stop overthinking it. I’m telling you that’s how life happens. Stop getting in your head about it and just make it happen. I think once you get over the resistance and the fear and you start making it happen, it gets easier and easier. I do what I do because I truly believe 100 percent we’re meant to be with somebody. I really believe that. And I think that a lot of us put fear in the way as an obstacle for resistance, and then you just got to get off of that and start running.

Charles: Sharon, how long ago did you move to Nashville?

Sharon: A year ago.

Charles: A year ago. How many churches did you visit before you decided to invest in the church that you attend now?

Sharon: Maybe five or six.

Charles: That’s a good number of churches. And it sounds like you actually have spent more time thinking about the church you want to attend, experimenting, and doing research, than looking for the person that you want to marry.

Sharon: Again, I keep coming back to that I want it to just be organic where I meet someone and we just fall in love.

Lisa: Organic is such a misconception. Historically we have been matched up by communities and religious groups. Urban environments have taken us away, and now we’re actually going back to the roots of connection. We’re going to online, to matchmakers, to churches. That’s what is organic. It’s not the other way around.

Charles: It’s interesting because I met my wife in college, and a lot of my friends met their spouses in college. And I don’t think for any of us it was love at first sight. And I don’t think for any of us it was organic. I actually don’t think for any of us it was easy.

Lisa: It’s a practical decision, right? That’s common.

Charles: A relationship is work. It’s a job. Even finding a relationship is a job. Once you’re in the relationship, it’s a job. It’s this thing that you decide to do together because you like being employed more than you like being unemployed.

Lisa: As we grow older, it takes more of an effort. I’ll give you an example. Someone who came to me was a 60-year-old man and he had never had a girlfriend. He was short, he was 5’3”. And in his mind he was a troll and undesirable and no one wanted him. And he was ready to move on with life and die single. And a lawyer friend of his said, “You know what? I know this matchmaker, Lisa Clampitt. Before you bury yourself in a coffin, go see her.” So he came, and what I saw is, first of all to me, he looked like a bigger guy. I actually took out a measuring tape. I was like, you’re not 5’3”, you’re amazing. He was funny. He was kind. He was brilliant. He was a self-taught violinist. What he needed is he needed to look at himself in a different way.

We spiffied him up, and I reprogrammed him from thinking troll to thinking funny, kind, self-starter, entrepreneurial. Unbelievable. So after months of working together, we found him this girlfriend and they’ve been together eight years. He looks like a movie star walking down the street. Unbelievable change of life—literally he came in with a little fanny pack and an old 1970s mustache, and was in a little ball of his misery of what he was projecting. That was his obstacle.

And so, Sharon, what are the barriers that you’re putting up? All these things could really turn around if you really wanted to. If you changed your mindset, I pretty much would say that you could be married within the next year or two.

To find out what happens on Sharon’s date, listen to the episode by clicking the player below or subscribing to How To! with Charles Duhigg wherever you get your podcasts.