The Millionaire Matchmaker, “Ayinde & Will”: eight with a brain

Ayinde & Will - hero

“Does the term a-hole mean anything to you?” – Patti

It’s yet another round of wedding planning to kick off the episode. Patti and Kristen the wedding planner visit Cakes By the Pound, and I’m already drooling thinking about how many pounds of that cake I want to… well, pound. As in eat quickly and in great quantity.

Check out our full and snark-tastic Millionaire Matchmaker episode guide and updates! Trash and treasure in equal increments, we promise.  

The Millionaire Matchmaker, “Ayinde & Will”: the clients and intro videos

The first client up to bat is Ayinde, a 37-year-old second generation Nigerian American and ex-volleyball player. “Ooh, he’s athletic,” Patti coos.

Ayinde comes across as super genuine and kind in his intro video, very different than many of the conceited weirdos that come across The Millionaire’s Club’s doorstep. Ayinde also explains that he’s been afraid of commitment in the past and wants to work on that in his next relationship.

And meanwhile we have Will Ratner, a 27-year-old “really good-looking guy” who is “about to inherit like $40 million,” Destin tells us. He’s also incredibly selfish and self-centered, via Destin.

Ah, that’s The Millionaire Matchmaker vibe that we’ve come to love!

Will introduces himself as an investment advisor and restaurateur in his intro video, and says “I live the lifestyle that most guys dream of.” He also said that in high school he used to “joke” that “girls wants to do me, guys want to be me,” and then follows up with: “It’s the same thing now.”

“He’s a total douche,” Patti quickly assesses.

Then Will goes on to talk about how quickly he can make the “panties drop” and you get the general vibe. “He’s Tom Jones,” Patti notes. Will then reveals that he’s cheated on women in the past and “can’t promise” that he won’t cheat again.

Patti expresses concern about using her service to set Will up with women… but she’s not quite concerned enough to not do it.

The Millionaire Matchmaker, “Ayinde & Will”: Patti meets the clients  

Patti meets Ayinde at a restaurant, and on route we learn that Ayinde is the CEO of Hitch Radio now that his beach volleyball career has concluded. He explains that his love life has suffered because he’s mostly around “tech guys” these days.

At lunch, Ayinde says he’s open to different kinds of women, but he wants someone who is spiritual, and atheists are a no go.

Patti digs into Ayinde’s commitment issues, and then says he wants to bring Dr. Nikki in to help him with that. Overall, it’s pretty clear that Ayinde is going to be the way easier client to deal with in this episode. Patti says that he’s the “perfect man” but there’s “one tiny speck of dust to clean up.”

Onward to Will, who Patti notes is a cheater, an a-hole, and a jerk. We learn that Will’s money comes from his family’s textile business. He talks about his woe in life is that women are after him for his money, but he needs someone who’s “top notch.”

At Will’s house, she asks, “Does the term a-hole mean anything to you?” It’s kind of hilarious that this question doesn’t phase Will at all.

After all of Will’s panty dropper talk, he now says that he wants someone with “career goals, you know, intelligence, any ethnicity.” Magnanimously, he then says he can “sacrifice a ‘ten bimbo’ for an ‘eight with a brain.’”

Patti seems impressed, but also thinks that maybe Will is telling him what she wants to hear.

The Millionaire Matchmaker, “Ayinde & Will”: the recruiting session   

Highlights of the mixer include Patti finding for Ayinde Aleesha, a journalist, and Joslyn, a business manager from Louisiana who is a former Miss U.S. (not to be confused with Miss U.S.A., apparently).

Things get more interesting in the recruiting session for Will. Patti likes Crystal, who owns an “exotic dancing” business but has ambitions to own a Subway franchise. Meanwhile, Michelle, a petite gal with braces, is termed “a little petite spinner” by Patti, who then asks her, “Did you get the breasts first or the braces first?”

And then there’s Rose, an office manager who Patti feels dressed inappropriately for the interview. “Hello boobies,” she notes before adding, “I don’t like when the bimbos are bringing the tatas to the table.”

The Millionaire Matchmaker, “Ayinde & Will”: Ayinde visits Dr. Nicki    

Dr. Nicki Monti asks Ayinde about his longest relationship, and then digs into his parents’ separation. He then reveals that his dad was murdered when he was seven years old.

Dr. Nicki tells Ayinde that he needs to “push through that wall,” and that not every relationship has to end as his parents did.

Ayinde seems like a really genuine person, and easily one of the most likeable that I’ve seen appear on The Millionaire Matchmaker.

The Millionaire Matchmaker, “Ayinde & Will”: the mixer    

The mixer takes place at Geisha House, one of Patti’s favorite sushi joints.

Will shows up late, and is chastised for being selfish. This confirms for Patti that he’s a “self-centered douchebag.”

When the mixers get mixing, Patti quickly assesses that while Ayinde is able to “connect with women on a deeper level,” Will goes into “player player” monologue mode. It occurs to me that Will looks a little bit like a poor man’s Colin Farrell.

Ayinde’s choices for the mini-date round are Aleesha and Joslyn, and Patti is thrilled with both. Will wants to get to know Nequisha better, who works in aerospace, in addition to “spicy” Rose. Patti is happily surprised and impressed with his choices.

Ayinde and Joslyn talk about family and seem like they have the potential to be a great couple. And then he and Aleesha get into spirituality. She says that she’s a Christian and unwilling to “dibble dabble” in other things in a relationship.

Meanwhile, Will gets a little interrogation-ish in his mini-date with Rose about why her past relationships went wrong. If you don’t believe me, here’s a quote from him: “What’s wrong with you? Why are you single?” Patti pulls him aside and says, “You’re so smart, but you’re so stupid socially.” Then things don’t go all that much better when Will mini-dates with Nequisha.

“No one’s gonna ride your ride,” Patti advises, if he doesn’t shape up. However, Will picks Nequisha for his Big Date and Patti still seems thrilled. Ayinde meanwhile had his “mind blown” by Joslyn and chooses her for Date #1.  

The Millionaire Matchmaker, “Ayinde & Will”: Ayinde and Joslyn’s first date     

Joslyn meets Ayinde and whisks her off on a helicopter ride for a tour of Los Angeles. She has never been on a helicopter and is excited.

They fly between the skyscrapers in downtown LA, and the couple crack up at “how Matrix it is,” which is rather cute. They go on to discuss their feelings about relationships. When Joslyn says that she historically has had long term boyfriends, Ayinde is surprised at how pleased he is to hear that.

Dinner is at a Moroccan restaurant, and Joslyn asks Will why he’s 37-years-old and single. Will says that he wasn’t ready to commit in the past but now he’s ready to settle down. Joslyn seems to appreciate the response.

And then a belly dancer starts to do her thing, and Joslyn gets up and joins her. This reminds me very much of my own wife, which brings back a story from when we first started dating: we went to a Moroccan restaurant ourselves, where indeed there was a belly dancer. My then girlfriend, now wife, prompted me to tip the belly dancer, and the dancer leaned over to me and said, “She’s a keeper.”

And she was 100% correct!

Ayinde seems absolutely delighted by the end of the night, and says that Joslyn “could be perfect.”                                                                                    

The Millionaire Matchmaker, “Ayinde & Will”: Will and Nequisha’s first date     

Nequisha rolls up in a Rolls-Royce that was sent for her. He tells her that he lives his life “over the top” and therefore needs to “steal” her for 24-48 hours. They pull up a private airfield, and take off in a private jet, and Nequisha is “floored.”

On board is Will’s attractive personal assistant, Ariel, who Will “always has to travel with.” She’s just as important to him as his Blackberry, he adds. Nequisha is not as floored by this.

It’s honestly hilarious to see the three of them sitting in a row in the back of the narrow airplane, with Will in the middle seat, popping a bottle of champagne as though he’s in the middle of some kind of pop punk music video.

In Las Vegas, they head to dinner, and Will explains that while other women at the mixer were more attractive, he picked Nequisha because she’s “mature” and “cool.” The floored level seems to be rising all the time.

Just when things seem to be warming up just a touch, date-wise, Ariel the assistant shows up again for reasons that remain unclear. At this point, Nequisha openly questions whether Ariel is actually Will’s assistant.

The three of them then hit the Vegas club scene, and Will tells the camera in a confessional that his dating style is “too crazy” for Nequisha. Evidently. Oh, and I must mention that a bunch of Will’s “homies” show up at the club to help celebrate Will and Nequisha’s first date as well.

The Millionaire Matchmaker, “Ayinde & Will”: post-dates upshot

Ayinde heads down to Patti’s office and tells her about the date. He also reveals that a second date is already on the books, where Ayinde will teach Joslyn to play beach volleyball. Patti of course is amped.

She then checks in with Nequisha, and Patti of course becomes less amped. “Nothing’s changed… he’s a total f—ing douche,” Patti concludes.

When Will gets to Patti’s office, she flat out accuses him of sleeping with his assistant. Whether or not that’s even true, the date was obviously a huge flaming Dumpster fire of a disaster, of course. Membership revoked!

The end of the episode captions reveal: “Ayinde took Joslyn to play beach volleyball. They are now officially dating.” And: “Nequisha and Will never spoke to each other again. Ariel is still working as Will’s ‘assistant’.”

The Millionaire Matchmaker, “Ayinde & Will”: where are they now?

The news about Ayinde and Joslyn officially dating is honestly one of the happiest moments I’ve had as a Millionaire Matchmaker viewer.

And… unfortunately it didn’t work out. However, it sounds like it was a positive experience overall, and meanwhile Ayinde Alakoye is thriving on the business side.

Some stats and info about The Millionaire Matchmaker – “Ayinde & Will”

TV SHOW – The Millionaire Matchmaker  
SEASON/EPISODE – Season 3, Episode 9
NETWORK/STREAMING SERVICE – Bravo
AIR DATE – March 23rd, 2010
GENRE – Reality TV, Dating Shows, Trashtastic TV
STARS – Patti Stanger, Destin Pfaff, Rachel Federoff, Ayinde Alakoye, Will Ratner  
NETFLIX DESCRIPTION – Will a commitment-averse client stump Patti in the matchmaking game? Can she reform a cheater looking to change his ways?  

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