If you don’t already know E. Jean Carroll, you ought to. She’s a master of men (she was Playboy’s first female contributing editor), doyenne of danger (she goes camping by herself. In February. At age 70.) and queen of questions (she’s got the longest currently running advice column in the country). She’s also my boss at Tawkify, the “dating concierge” service she started in 2012, and she’s taught me everything I know about matchmaking.

My first week on the job when I had a client that had rejected every man in lower Manhattan I consulted her for advice. “Tell her she’s beautiful and keep her expectations at rock bottom,“ she told me. "Then bang ‘em together and see what happens.” It worked. Later, when I was having my own romantic turmoil, E Jean handed me a glass of champagne, looked me in the eye and gave her prognosis: “You’re young. He’s a waste of time. Onwards!” Finally, when I started writing this column, she memorably said to me: “Hugh Hefner did more for women then Betty Friedan!” before pulling me close and whispering in my ear, “As an advice columnist you live and die by your questions, Katherine.” Thanks to E and to all of you, I feel more like I’m living than dying. And this week I decided to bring the “questions” to her.

We shared a glass of wine (or three) the other day to discuss the delicate art of the setup. Swiping right works for some but for those of us who prefer a human touch, how do we proceed? Or Is "the setup” a dying art? E. Jean doesn’t think so and she’s got the credentials to prove it. I know many happy couples who’ve met through blind dates and yet it can be anxiety-producing to be the one executing the setup or the one who’s stepping out on faith. Thus, E Jean and I are here to share with you our thoughts on the delicate art of the set up and how to execute it with panache.


What are the most important things to remember when you’re setting somebody up on a date?
1. You are mother nature’s ally. You can bang two people together but you can’t make their pupils dilate. You can’t make his voice drop; you can’t make her breasts swell. These are the physical changes that happen when people see somebody they like. You can introduce them, that’s it.

2. Don’t ask questions about what the person you’re setting up wants. You don’t want to give them what they want. You want to give them what you think is best.

3. Keep the mystery. Don’t reveal anything before they meet. At least nothing Google-able. If they Google each other it’s over before they even meet. This is particularly true of this guy I’m setting up right now because he’s got a bad reputation. He’s a man about town.

As in … a playboy?
Yes. He has the most beautiful dinner jacket, cut to a faretheewell. He showed up to dinner in it the other night and I could not find human speech for 10 minutes.

So, what are some other common pitfalls of setting people up?
Don’t let your ego get involved when you’re setting people up. Especially when you know the people well.

What do you say to people before you set them up? Try not to get to know each other too well. It got Oedipus into big trouble.

And then where should you send the people you’re setting up?
1. The Russian Tea Room. The golden lighting will make you fall in love with whoever you’re sitting with.
2. Playing darts. Breeds healthy competition.

…and nobody’s great at darts.
And if they are you should be suspicious.

3. On a “Penis Scavenger Hunt” at a museum. Go to the Greco-Roman wing and give them thirty minutes to find ten penises. If that doesn’t get them in the mood, I don’t know what will.

That’s a lot given how many are covered up. Do fig leaves count?
Fig leaves are worth half a penis. We’ll call it “the fig leaf tour.”


What should you keep in mind as you’re dressing for a date you’re being set up on?
Just wear the best thing in your closet.

But what if it’s too formal?
Who cares. If you’re a guy, show up in a suit. A morning suit! Like Hugh Grant in Four Weddings and A Funeral. We all love that. When a man show’s up in a suit he’s way ahead of the game. I don’t care if you’re going iceskating: wear a suit! A woman’s clitoris begins quaking when a man shows up in a suit. Isn’t that true, or am I nuts, Katherine?

E. Jean Carroll

E. Jean Carroll

You’re certainly not nuts. But quaking? That’s got to be some excellent tailoring. This is not a Men’s Warehouse suit we’re talking about. I think shoes are the new suit though. I’ve noticed that a lot of women are scoping out men’s footwear.
It tells you his income and education level…

… And if he’s somebody that walks places or takes cabs everywhere, if he gets dirty or stays meticulously clean.
But if he’s wearing a suit none of it matters! We’re simply higher primates so we read shapes. Women read broad shoulders. They read the package in front. And we don’t even know we’re checking it out. And that’s the main reason you’re looking scanning down to look at those shoes. A man should get a bespoke jacket just to wear on dates.

OK, so here’s something I struggle with sometimes. What do you think you should say to yourself in the mirror before you go on a date you’re being set up on?
Don’t look in the mirror. Your fantasy of yourself is always better than what’s there. Also men, should definitely get ready for a date listening to the Superman theme music.


PS: Join me on Playboy’s Twitter next Wednesday at 2 PM EST / 11 AM PST. Bring your questions and tag them with the #JustTheTips hash-tag.

Just the Tips is Playboy.com’s weekly advice column, with professional matchmaker Katherine Cooper. Have a question for Katherine about sex, love or dating? Shoot her a note at justthetips@playboy.com.