The Wingman Cometh: Jewish Matchmaker Addresses ‘Shidduch Crisis’

In the risky business of coaxing love, the Wingman was flying without a net.

At the sleek Pop Lounge on East 58th Street, Aaron Ellner, aka The Wingman, was hosting one of his singles parties, trying to do his part to address the so-called “shidduch crisis” in the Orthodox community.

And he had an ace up his sleeve, a sure-fire conversation starter.

His client, a 25-year-old, Modern Orthodox insurance salesman from Long Island, needed a little nudge. So as the party was winding down, the Wingman introduced him to someone he already knew, a 25-year-old Modern Orthodox woman from Staten Island. And he slipped into the conversation the fact that, believe it or not, she’s a trapeze artist.

The ice now broken, the salesman took it from there, made the trapeze artist laugh, and the two have now gone on several dates.

“I’m not entirely sure I would have gone over to her on my own,” the insurance salesman said. “Aaron’s icebreaker really helped.”

Score one for The Wingman, one of the few Jewish male matchmakers in town.

In a Jewish singles world dominated by women matchmakers, from the iconic Yenta in “Fiddler on the Roof” to Shoshanna’s Matches, Ellner, a 24-year-old graduate of Queens College who lives in Woodmere, L.I., launched his website, www.thedatingwingman.com, in March. And despite his relative youth he claims some knowledge when it comes to the secrets of romance.

Ellner, who says most of his clients are Modern Orthodox and to the right of that (though some are less observant), refers to himself on the site as a “dating consultant.” His calling card, as it reads on his site: “The very first minute of meeting someone may be the deal breaker. I will instill confidence by giving you my personalized advice that will bring out your best inner self.”

But what sets him apart is his willingness to be a wingman at parties, to see his clients in action up close and offer advice on the fly.

“It’s a great mitzvah to set people up and usually, the [matchmaker] has the best of intentions,” said Ellner, who doubles as a substitute teacher in the public schools. “But when you set people up because they are both tall, or because they both have the same occupation and you don’t really know anything else about them, you’re setting the person up for failure.”

Ellner says he tries to set people up for success by having a consultation ($60 an hour) with them or by seeing them in action at one of his parties. Ellner, who will host his next party on June 24 at The Hill on Third Avenue, says his approach is more effective than matchmaking sites where singles are set up based on an online profiles or a phone conversation. The real test is to see clients up close, hence the “wingman” moniker. He said he is there to pump up a guy or girl who is about to begin a conversation.

So how does Ellner, at such a tender age, know what they should say? Besides being around friends who are dating, and drawing from a nearly decade-long relationship, he says sociology classes helped him learn a lot about human behavior. And he tells both males and females to avoid one approach that could nix the chance to score a first date.

“It’s surprising to see how many people bring up negative things about themselves,” Ellner said. “I’m all for being honest, but you don’t need to put all your cards on the table in the first conversation. My rule is to stay positive and once there is that attraction, that information can be revealed later.”

Lauren Lillien of Cedarhurst, who recently ran a singles night at Ohr Torah in Woodmere, said she was happy to have Ellner help at her event.

“I think one of the reasons you only see female matchmakers is that some guys are creepy,” said Lillien, who is single. “But Aaron is a cool and good-looking guy and he is really able to make people feel at ease, disperse through the crowd and give advice. He has a knack for it and it’s something most people probably couldn’t do so well.”

One 23-year-old male, who attended the same party, said he was impressed by Ellner.

“I was shocked,” said the Brooklyn College graduate. “He looks nothing like a matchmaker. Think of it this way. He gives you the 411 on someone’s religious level and their job or whatever your main thing is, so you have a sense of what you’re going into.

“Aaron can give guidance and also save you a lot of potential embarrassment and heartache.”

Says Ellner, an avid skier who is newly unattached after a long relationship: “Almost everyone has something about them that’s intriguing and impressive. But people don’t bring it up because they don’t want to seem like they are bragging. With a wingman or friend with them, that person can mention it and [have] a more organic and more natural conversation.”

He added that some people are reluctant to have their friend as the wingman or wingwoman because there is a fear that the friend will want the guy or girl for him or herself, causing a strain on the friendship.

The Wingman’s best piece of advice for singles — stay in the game.

“You’ll have a client who’s had a few bad experiences,” he said. “They’ll turn to their friends and say, ‘What am I doing wrong?’ Their friends might not know the answer, or they might not be in a position where they can be honest. I can be honest with them, but in a way that builds them up instead of knocking them down.”

Ellner’s sense of guys helping guys through the dating process is one echoed by another male matchmaker, Steve Eisenberg, co-founder of the Jewish International Connection for New York or JICNY. Eisenberg, who said he has made about 75 matches, considers himself an unofficial matchmaker.

“Males could have an advantage helping other males because of familiarity,” Eisenberg said. “But at the end of the day, it doesn’t matter if you’re male or female and your age doesn’t matter. What matters is that the person is sincere and has a sense of two people that would click. What is also crucial is that there is follow up and guidance while they are dating.”

Which is what the Wingman specializes in, and it’s paid off to an extent. Since launching his site three months ago, Ellner, who is reluctant to say how many clients he has, says eight couples he set up are currently dating.

“People have always told me I should be doing this and now I am,” Ellner said. “I am focused and dedicated to helping people find their beshert, and there’s nothing better than that.”

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