Getting Ready for Love

I once went to the movies on a date with a guy who didn’t pay for my ticket, and didn’t offer me a snack as we approached then walked right past the popcorn line. When we got to our seats he opened his jacket – he had brought himself a drink (Snapple) and a snack (bag of chips) from home, of which he offered me none. His attitude was clearly, well I’ve got my stuff. Where’s your stuff? These are the Prince Charmings I’ve dated.

When I met matchmaker Claire Wexler, the first thing I loved about her is that she’s single. Gorgeous, funny, smart, and single. If she were married, I’d think, of course she’s married because everyone’s married, I’m the only single one, I’m sick of trying to find my soul mate love and I’m going to just quit. But if Claire Wexler – who has been a real-life matchmaker for 12 years; who is the vice president at a top-notch matchmaking firm with the professional and full-proof-sounding name Selective Search; who spends every day meeting single men who want to meet single women – if she is still looking for her one true love, then I’m going to keep looking too.

I asked Claire to sit down with me and talk about how I should go about getting ready for love. I’m already working with Dr. Laura Berman, renowned love coach, sex therapist, and a great friend who is guiding the STORY team on our quest to find the men of our dreams. But I thought it would be interesting and revealing to talk to someone who is in the trenches of the dating world, someone who would give me an unvarnished account of what it’s like for women out there these days. Someone who would pull no punches.

NANCY: I’m fascinated by matchmakers. I think that a personal, curated approach to dating is like hiring an executive search team to find the perfect job. Do you love what you do?

CLAIRE: I really do and I came by matchmaking very organically. I introduced my father to his second wife. I began my career as a full-time matchmaker in New York, where I generally worked at finding prospective matches for men. I joined Selective Search 12 years ago. We work with about 500 clients across the country, and 85 percent of them are men.

NANCY: I bet you hear a bunch of stories from your male clients about the women they’re dating.

CLAIRE: Oh yes.

NANCY: What are the biggest mistakes women make when they decide to dive into dating again after, let’s call it, a long pause?

CLAIRE: I think that women can be negative on dates, talking about their failed relationships or dating mishaps. Or they tend to over-share right off the bat. It is not necessary to tell someone everything about yourself in the first few hours, or even days, of meeting them.

NANCY: No need to download it all right away.

CLAIRE: Exactly. Also, I personally don’t think people should have sex too soon. Listen, after a long dry spell you might say, hey I really want some sex. The problem occurs when women equate sex with intimacy. It comes down to different expectations. You can’t force intimacy, that happens over time. I tell my clients to take things slow, get to know each other. You can make out to see if you have chemistry, but don’t feel pressured to have sex.

NANCY: Do women my age – I’m 53 – actually feel pressured to have sex? That seems like something that happens when you’re much younger.

CLAIRE: Well they say, “I don’t know what he rules are now.” And I tell them, “Do what feels comfortable to YOU.”

NANCY: That’s always good advice.

CLAIRE: I think there should be a conversation first. Ask the guy if he’s looking for a monogamous relationship. If he’s seeing other people. I find that people often don’t ask the questions they don’t want to hear the answers to. You have to ask. You should never make assumptions about the way someone else is thinking or feeling.

NANCY: It’s hard to have those conversations. I remember dating a guy for about two months before I asked him if we were exclusive. I assumed we were. I had met his family, we were seeing each other two or three times a week. I was really only asking as a confirmation. He casually told me that he was seeing “two or three” other women besides me. I was stunned. I didn’t know what to say. I was like, two or three? Which is it? Can I at least get a headcount?

CLAIRE: Like any rational person would, you assumed based on his actions that you two were in a monogamous relationship, but unfortunately you waited too long to have the conversation and ended up by getting hurt.

NANCY: It was like all the joy just got sucked right out of the room. One minute I was part of a happy couple, then next I was one of four women he was seeing. So I agree, you’ve got to have those conversations early, but I think it’s hard to know when to do that.

CLAIRE: It is. It’s hard to open yourself up and feel vulnerable. You’ve got to really practice honesty and clear communication. You have to get the answers to the questions that are important to you. You need to get comfortable with letting men know you are expecting monogamy, if that’s what you’re looking for.

NANCY: So I’m just going to come right out and ask this – can a woman in her 50s find love?

CLAIRE: Oh absolutely. We work with so many women in that age group that get married or end up in a happy partnership. Look, 50 is much younger today than it used to be. People are taking better take care of themselves. Women in their 50s have a lot of life experience, and they have so much life yet to live and they want to share it with someone. Men who have had life experiences of their own, who have had a career and success, they can talk to women their own age. They can relate.

NANCY: What is the age range a woman in her 50s should be targeting when she’s looking for a man to date?

CLAIRE: Women should look at their own age and up to 10 years older. That’s very realistic. Maybe a couple of years younger.

NANCY: What are some tips a woman can use to improve her odds of finding great soulmate love?

CLAIRE: The number one most important thing is attitude. One concern men have about older women is that they will be jaded or too set in their ways. Or not able to keep up – I hear this all the time from men.

NANCY: Not able to keep up? You’re kidding me. What are these guys doing that’s so hard to keep up with?

CLAIRE: I know –

NANCY: Are they all running marathons and climbing mountains?

CLAIRE: I know! But men who are fit and active are afraid women their own age won’t be able to keep up. They want someone who’s leading a healthy, active lifestyle. The thing is to be the best version of yourself. Be fit and healthy, passionate and interesting. Be a lifelong learner. Amplify what you really like about yourself. Be playful, have a sense of humor. Deal with your stuff, don’t be dragging around baggage. When you feel good about yourself, everyone wants to be around that.

NANCY: Ok, so be athletic, fascinating, smart, playful and funny with no baggage. Got it. That’s super easy. Let’s come at it from a women’s point of view – are there new dating red flags we should be watching for? Male behaviors we should know to avoid?

CLAIRE: Probably the same ones from before! Like, someone who doesn’t ask you anything about yourself, who spends the whole date in a monologue. Or shows up late and doesn’t apologize. On the other hand, I say give people a second chance. First dates can be nerve-wracking. If the first date was just ok, go on a second date. You’re looking for a connection. On the first date if there’s a glimmer, give it another shot.

NANCY: Claire Wexler, matchmaker and modern day yenta, do you believe in true love?

CLAIRE: Doing what I do totally affirms my belief in love, because I see it all the time. If you stay in a place where you’re happy with yourself, you will find it. You have to believe in your own value and never sell yourself short. Come from a position of strength. Maybe you’re an amazing mother, a fantastic sister or loyal friend. Know that you’re a catch for the right person. Be the best version of yourself, have a great attitude, and go for it.Claire Wexler is VP of Client Services at Selective Search®, a leading luxury matchmaking firm, where executive recruiting meets personal matchmaking. Founded in 2000, Selective Search is North America’s leading boutique matchmaking firm, with clients and affiliates throughout North America and abroad.