“How To Date A Wall Street Guy” Matchmaker Actually Has Decent Dating Advice

Such as: don’t act like a jaded sad sack on a first date.

Matchmaker Samantha Daniels gained some internet notoriety this year when she posted a story on CNBC around Valentine’s Day called “How to Date a Wall Street Man, which offered tips like, “[Y]ou shouldn’t be difficult. You need to be accommodating for his schedule and time constraints or he will get frustrated and find another woman.” And: “Don’t get upset if he checks his BlackBerry or takes a call during a date.” Last night, at an event for around 30 well-heeled single women at the Pierre Michel Salon on Manhattan’s Upper East Side, Daniels explained that it’s not like she endorses this kind of thing. “Do I approve of their behavior and the things that I wrote? Of course not,” she told me. “But I wasn’t pro and I wasn’t con — I was basically just providing information objectively, and saying that I’ve been in business for 13 years as a professional matchmaker and relationship exert that specializes in very high-profile, successful men, and many of them work on Wall Street, and these are some of the things that they’ve told me. So if you’re a woman who wants to be with this kind of guy, then here are some tips for you.”

The women at Daniels’ event were eager for her advice — some of which, if you really consider it, truly isn’t bad.

Before her talk last night, Daniels introduced herself to each woman there, and complimented everyone on something about their appearance. “I love your pants. Are those Nantucket red?” she asked the girlfriend who came with me, who was wearing a pair of trendy red skinny cords. “That’s how I remember people—I remember something they’re wearing,” Daniels explained. She then told my friend to take a picture and register on her site so that she can possibly get set up with one of Daniels’s clients. (These events serve as symposiums for Daniels to advise women, but also function as recruiting grounds.)

Attire figured considerably into her talk when she started giving out dating tips. “I’m looking around the room and over half of you are wearing black,” she said. “I swear to you that men tell me every single day that they are not attracted to women who wear black. They think that women who wear black are depressing. They think that women who wear black look older than they are.” Audible gasps were heard around the room.

One lady interrupted Daniels to say that she was wearing black right now and it was always a good date look.

“Well, because your shirt is completely see-through,” Daniels said without hesitation.

“There are exceptions—” the woman protested.

“I mean, if you come naked but you’re wearing black lingerie” — men are obviously going to like that, continued Daniels (who told me she routinely turns down requests to do reality TV). She suggested women try red or pink or floral print. (Her favorite color, which she wore last night, is purple.)

Not a date look.

Daniels also advised women to be careful if they’re meeting men on Thursday nights because that’s when a lot of married guys go out. “When you’re meeting men on Thursday night, you have to get to the heart of the question and finding out if they’re available, because married men get their rocks off by talking to some fun, sexy, young single girl because they want to live vicariously — they don’t realize that they’re wasting your time,” she cautioned. She notes that you can often find out if a guy is married without asking directly, by asking indirectly: “You know, ‘Where is your family?’ ‘Oh, in Greenwich.’ Chances are, he’s married. Or, ‘Oh, do you have children?’ ‘Yes, I do.’ ‘Where is your wife tonight?’” Etc.

Her other big pieces of advice were to be positive on the first date, and not drone on about emotional baggage or act like a jaded New Yorker. “At the very beginning, you need to lure him in. You need to put that bait out and you need to make him want to want you, and then later on, when he falls for you, whatever your crap is, he’s going to deal with it,” she explained. “If you don’t put your A game on that date, you’re not getting a second date. Because he had a date the night before you and he’s having a date the night after you.” (Of course, the same is true for men — no one wants to hear someone drone on for hours about their issues, whatever their gender.)

Daniels claimed that women often wrongly assume a man is only seeing them. “I can’t tell you how many women say to me, ‘I know that we’re exclusive. I see him every Saturday night, he’s sleeping with me, I know he’s not sleeping with anyone else. I’ve met his friends, I’ve met his family, I know we are exclusive,” she said. “You do not know that you’re exclusive with a man until you have a discussion with him and until he looks you in the eye and tells you that you’re exclusive. And even then you don’t really know, which is pathetic in and of itself. But I can’t tell you how many men come and meet with me and the first words out of their mouth is I’ve been in a relationship with a woman for a year-and-a-half, but she’s not the one that I want to be with, but I’m with her because I like to have someone to go out to dinner with, we go on vacations together, and I take her to my work functions.”

More fun with stock photography.

Daniels’ outlook can feel rather antiquated, in that she targets it specifically to women — as though we are always the ones who should be chasing these “awesome” guys. It’s not bad advice, per se, it’s just that it should apply to both genders. After all, would you want to go out twice with a guy who spent your first date acting like he hated the world? And would you want to go out with a guy who didn’t want to try to make you want him? And if you were sort of keeping someone around for sex and the occasional date, but nothing very serious or long-term, and never had a conversation about exclusivity, would you necessarily assume he knew you weren’t exclusive?

Didn’t think so.

Samantha Daniels is the author of Matchbook: The Diary of a Modern-Day Matchmaker.

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