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This week on ‘Millionaire Matchmaker’

Allison Hoffman
April 07, 2010
(Bravo TV.)

Every Wednesday, Senior Writer Allison Hoffman recaps the previous night’s episode of the glory that is Millionaire Matchmaker. For previous Matchmaker coverage, click here.

There comes a time in every young boy’s life when he finds himself at the threshold of becoming a man. Symbolically, that happens for Jewish boys when they turn 13. But in reality, it comes later. Much, much later. Sometimes, never. But that’s where Patti Stanger, the Maharat of Matchmakers, comes in.

So, let’s meet this week’s overgrown children! First we have Dylan Smith, the 24-year-old CFO of Box.net, a cloud-computing service he started with a friend while he was an undergrad at Duke and now runs from offices in Palo Alto, California, where everyone else is, like, 30 and married. Dylan has many things going for him: Along with being a venture capital-backed paper millionaire—the next Mark Zuckerberg, maybe!—he is an avid half-marathoner and a Wiffleball champ and also a committed member of a Rock Band. (As in, the video game.) In fact, Dylan has so much promise that a companion wondered why the kid couldn’t just wait a few years for the hot Russian women to start throwing themselves at him in nightclubs. But, see, the problem is that he’s not getting laid at the moment, and that is what he wants Patti to fix.

Next to angelic Dylan, 28-year-old Hillel Presser looks, frankly, over the hill. But he comes from “the land of Florida,” as Patti puts it, and he’s had to work for his money: He’s an attorney in Boca who specializes in “asset protection,” which is to say, in hiding money from angry exes and jilted business partners. A noble cause! In his spare time, he invests in a company called 1-800-Muffins, which appears to be absolutely exactly what it sounds like. Hillel, who has short, gelled hair and a bit of a gut, volunteers that there is nothing in life that he wants but does not have, except, of course, a girl who looks just like Sloan from Entourage. “I just want a nice girl who likes me for me,” he tells Patti earnestly. “And I wanna be attracted to that girl.” That old chestnut!

“Just because these guys aren’t major assholes doesn’t mean this week’s gonna be easy,” Patti confides. But she’s got some tricks up her sleeve! One of them is a blonde named Michelle, a Hooters waitress looking to upgrade to porn. “I think it would be an honor to be a Playmate,” she tells Hillel, who responds with a blank nod. There is also Farah, a retread from a prior episode who works in marketing for “a beer client.” Perfect! For Dylan, meanwhile, there is Arielle, a brunette who looks a little tired for 24 but who says she’d like to run with him every day of her life.

The trouble with Arielle is that she turns out to be a little … judgey. See, Dylan is the kind of guy who shows up for a reality TV dance class wearing moose-printed pajama pants. He gets tongue-tied in his confession moments, and he talks about his childhood hamsters—who were majorly in his life until, like, not that long ago—and he can’t help himself from saying things like, “I didn’t have any specific algorithm in mind to compare Farah and Arielle.” It’s kind of endearing! But Arielle is not so impressed. Dylan tells her he graduated from Duke late because he took time off from school. “To become a shmillionaire?” she interjects, apparently forgetting the entire reason she is on this date in the first place. Tragedy! Although Patti has given Dylan special permission to kiss Arielle, he spends the whole date—at an emptied Hollywood club called Cafe Was—angling for a chance to execute that strategy instead of just being himself. “I did kiss her! I did not ask!” Dylan reports back, when he goes for his debrief with Patti. Baby steps, young grasshopper!

While all that’s happening, Hillel is up in the air with his date Farah. In a weird continuation of last week’s Pretty Woman theme, he flies her to San Francisco in a private jet for dinner. On the way, he hands her some muffins. “She just shoved that muffin in her mouth!” Hillel exclaims, clearly wondering what else might follow. But Farah seems more excited about the accoutrements than about her putative Prince Charming. “I got to ride on a plane!” she exults once they land. (“Not ‘I got to ride with you on a plane,’ ” noted a friend of Scroll). And poor Hillel, who told the cameras he thought Farah was the kind of girl he could see himself marrying, starts to lose his footing. Thankfully, he’s got a crutch: booze! Yes, he tells a waiter at the Mandarin Oriental, please keep the drinks coming. “The more she drinks, the better I look,” he theorizes. Eventually they go up to the roof to admire the city lights, and he decides that he, too, will go in for a kiss. But all he gets back is a quick peck, as Farah recoils. Hillel, it seems, will return to Boca as the same boy.

Except then something weird happens: When he goes to see Patti, he tells her that he and Farah had dinner in L.A. the night before … “And then I had lunch with her again today.” Interesting! “It turns out Farah was not looking for Brad Pitt, but was looking for Hillel Presser,” Patti says, optimistically. We’re not quite sure, but it’s a nice thought.

Next week: the season finale, featuring Zagros, the guy who was last seen paired with Uri, the Israeli obsessed with “spinners.” Can’t wait!

Allison Hoffman is a senior editor at Tablet Magazine. Her Twitter feed is @allisont_dc.