Forty First Dates and Still Searching

On a balmy Thursday evening in late July, Joseph Pascaretta, 38, got ready for his fifth first date of the summer. He put on his signature first-date look: jeans, a collared shirt, dark sport jacket. The vibe he aspires to, Pascaretta says, is Eugene Levy — from the suits to the eyebrows.

Pascaretta walked into Dear Irving, a dimly lit lounge with Art Deco décor in the Gramercy neighborhood of New York, 20 minutes early. He chatted with the hostess, vetoing the first table he was offered in favor of one close to an old record player he thought might be a conversation starter.

Pascaretta’s date that night — a petite 30-something brunette with a wide smile — arrived 10 minutes late. Annoying, but not a deal breaker. She promptly ordered a martini, so Pascaretta, usually more of a wine guy, got a Crown whiskey and ginger ale, his go-to so he doesn’t have to fuss too much over the drink menu.

Right away, the date felt flat to Pascaretta. He is an executive at a global software company specializing in industrial artificial intelligence. His date had a big job in financial services. They were both professionally adept schmoozers, so over two rounds of drinks, they covered a lot of ground: the summer wedding circuit (she is a maid of honor in three, a good sign, Pascaretta thought); politics (both Republican); the Knicks; Celine Dion (she is a fan, and he’s going to her concert this fall in Paris). But there was no sizzle. After three hours, Pascaretta walked his date back to her apartment, where they hugged briefly. No kiss.

Six days later, Pascaretta dialed into a Zoom meeting with the woman who had set him up on the date: Maria Avgitidis, the founder and chief executive of Agape Match, the high-end matchmaking company he had hired to help him find the love of his life.

“On paper, she was a match,” Pascaretta told Avgitidis, the Empire State Building visible from the oversize windows in his Chelsea apartment. Avgitidis, who lives in New Jersey with her husband and their two children, had dialed in from Greece, where she spends part of the summer with her family. Her sister Chrisoula Mavrianos, 40, a senior matchmaker at the company, puttered around in the background, joining the call at several points.

“I don’t know,” Pascaretta told the sisters. “There was something that was … off.”

Pascaretta’s contract with Agape Match guarantees him at least one date per month from the company’s mblockive database of single women — most of whom have signed up for free, uploading a photo, filling out a questionnaire and then sitting for a 60-minute “discovery call” where the matchmakers quiz them about everything from their ideal date to their political views.

Over email in July, Mavrianos sent Pascaretta three women she wanted to introduce him to, all in their 30s: a finance professional from Wisconsin who is a die-hard Packers fan and volunteers with the Junior League. A lobbyist and military veteran who loves to garden and travel. And a digital strategist with blond waves down to her waist who, like Pascaretta, is a University of Michigan alum. All three were so conventionally pretty, their profile photos could have easily been casting headshots for a new season of “The Bachelor.”

“Yes to all three,” Pascaretta wrote back. “Amazing, wonderful profiles!”

Why not? He was four months into his six-month, $25,000 contract with Agape Match, so he still had free dates coming. He still felt optimistic that something would work out. If you counted his previous two arrangements with the company, going back nine years (with a pause during the pandemic), he had paid the matchmakers roughly $65,000 and gone on approximately 40 first dates, and 20 second dates — only one of which led to a relationship. (With a stunning surgeon who graduated from Harvard, but she was fresh off a divorce and still figuring things out.)

Pascaretta saw the money as a reasonable investment in what he believes will be the single most important decision of his life. Yet he acknowledges he has been bruised by dating, just like anyone who has been at it for years. Lately, he has been having a harder time letting go of his disappointments — carrying a kind of niggling self-doubt into some of his dates. And he feels a sense of urgency now that he did not during his first and maybe even his second contract, he said, when he probably wasn’t as serious about finding a lifelong partner as he could have been.

“If you called me eight years ago and said, ‘Do you think you’ll be single by 38?’ I would have said, ‘Oh no,’” he said. “This is getting a little old. Some of this is not fun anymore.”

Pascaretta thought he would be married by 38, maybe a father. He is a family guy, godfather to four of his nieces and nephews. He takes regular vacations with his cousins, and always took it on the chin when his beloved Uncle Nunzio teased him that he is like a grapefruit, slowly going bad. Pascaretta certainly sounds like an old timey sitcom dad, peppering his conversations with exclamations of, “Geez-o-Pete’s” and “son of a gun.”

He has some theories about why he hasn’t settled down. His grueling work schedule is one. Pascaretta travels almost every week for work, often to Europe, and frequently signs on for the day around 2 or 3 a.m. before the markets open.

And there is his height. Pascaretta, who said he is 5-foot-6 (“5-7 on a good day”), knows it can be a deal breaker for some women — certainly on the dating apps. “That’s a big deal for some of these girls,” he said.

A match he recently went on a few dates with mentioned, while they were at dinner, that she wanted to be with a tall guy — even though the team screens for women who are open to shorter men.

“I’m like, You’re 5-foot-1! I’m tall compared to you,” he said. “It made me sensitive to it.”

Pascaretta has dabbled in the apps casually, thanks to a few colleagues who set him up with profiles on Hinge, Bumble and The League, but he thinks they’re superficial. Strictly a numbers game. Matchmaking may sound like “voodoo” or “witchcraft” to some of his friends and family, he said, but he feels there is nothing like having a team of people who understand you out there searching for Mrs. Right for you, hyping you up.

Pascaretta has lofty standards. When he signed his third renewal, he sent the Agape team a six-page Word do***ent with details about his past girlfriends and a one-page self-profile. “I’m a rare blend of executive discipline and genuine warmth,” he wrote, mentioning his M.B.A. and pilot’s license. He also “cooks and cleans like Mrs. Doubtfire,” Pascaretta noted, “by choice, not necessity.”

“Grounded in my Italian roots, I lead with heart, drive and zero ego,” he wrote. “I’m looking for my queen — someone to grow with, not just go with.”

Pascaretta also sent the team an Excel spreadsheet cataloging his must-haves: an accomplished professional, ideally a doctor, lawyer or executive, “someone like me who has been ‘heads down’ career focus, but now is ready for a serious relationship.” Someone who has never been married or is at least amicably divorced. Someone shorter than him. And someone between the ages of 25 and 43. It also detailed his strong preference for a woman who is, among other things, “naturally pretty” and “stylish,” “loyal, clblocky, ambitious, elegant, feminine, emotionally stable,” from a “well-respected family” and who went to a top-tier school.

He has, at times, been frustrated with his lack of progress. Once, Pascaretta snapped at Avgitidis that he would have better luck just putting his name and number on a billboard. He even researched the cost: $1,800 for six hours during rush hour outside of the Lincoln Tunnel.

“What I was trying to figure out with Maria was: What are they looking for on the first date?” he said. “Because we keep having this first-date syndrome. ‘Oh, he’s great. He’s dressed sharp. Amazing. But I didn’t feel the connection.’”

Avgitidis has worked as a matchmaker since her early 20s, but she feels as if something has shifted among daters in the last year. The apps have worn people down while simultaneously giving them the sense that they have unlimited options. At the same time, social media is awash with talk of green flags and red flags and dating absolutes. Throw in the astronomic rise of A.I. chatbots designed to endlessly flatter and reblockure and there are a whole lot of daters now who have begun to mistake compromise for settling, Avgitidis lamented.

However grim the dating environment, it remains unusual for someone to turn to a matchmaker when looking for a partner. Amanda Gesselman, a research scientist at the Kinsey Institute in Bloomington, Ind., who works on the organization’s annual Singles in America Study (in blockociation with the Match Group), said only around 1 percent of respondents had indicated they used a matchmaker since the survey started asking in 2012. An estimated one in 10 Americans still meets their partner on an app.

“People don’t realize it’s an option,” she said, “and if they do, it’s because they’ve seen shows like ‘Millionaire Matchmaker’ so they think it’s only for ultra rich people.”

This summer, Agape Match had 15 current matchmaking clients — a fairly typical load — all men, except for one woman, which is unusual for the company. Avgitidis has found her niche with straight men — partly because she finds they are the most receptive to her often blunt feedback, and partly because of her database of singles. She has found it easier to amblock a large group of attractive, successful and datable women than an equivalent large group of men.

On a team Zoom call in late June, the company’s four matchmakers pulled up client profiles one by one. At 41, Avgitidis is an elder millennial, but she can come across as an outspoken and involved grandma who just wants everyone around her to be happy and settled already. Indeed, she thinks well-intentioned meddling is exactly what is missing from modern dating. People used to get set up by friends and family, Avgitidis says. They’d meet at a cookout or a house of worship or flirt for hours at a bar. Now, their primary means of connection is mindless swiping, she said: on the couch while half-watching a TV show, standing in line at Starbucks, even sitting on the toilet.

“Dating right now has become an incredibly lonely activity,” she said. “It used to be a community endeavor.”

Several times during the team meeting, she grew frustrated with her clients’ high standards, throwing her carefully manicured hands up in the air in exasperation.

There was the 40-something doctor who had just gone on a Zoom date with a 31-year-old pediatric nurse practitioner educated at Duke and Johns Hopkins who, in her profile photo, looked kind of like Kate Middleton. She was nice and “very pretty,” he reported back, and they had a nice conversation, but she wanted to live in the city and he didn’t. He was on the fence.

The matchmakers also puzzled over the Ivy League-educated economist who said he wants to date only women who are thin, have large block and are fluent in Mandarin, but who should not have any artistic hobbies or talents. He had been unable to fully articulate why. Avgitidis — who takes pains to understand her clients’ family dynamics and cultural backgrounds (she’s from a close-knit Greek family herself) — suspected it had to do with parental expectations.

Eventually, the team turned to Pascaretta.

“He’s a 50-year-old man in a 30-year-old man’s body, and the kind of woman that’s going to be with him is the kind of woman who envisions herself being the wife of a congressman,” Avgitidis said. “She needs to be someone who is extroverted, or understands how to work a room. Because he is the person that works the room.”

“Chrisoula and I feel very frustrated by some of the women, because we cannot comprehend why they don’t want a second date with him,” she continued.

They say, “‘He’s lovely, I just don’t envision him as my husband,’” her sister piped in.

“I’m like, ‘Why are you thinking about that on a first date?’” Avgitidis said, waving her hands in the air again, a small cursive “love” sculpture behind her, across from a copy of her book, “Ask a Matchmaker.”

“The purpose of a first date,” she continued, “is to go on a second date.”

Earlier this summer, Pascaretta thought he may have just found The One — a TV news correspondent he dutifully watched in the mornings, and whom he thought was gorgeous and smart. He mentioned her to Avgitidis, who checked: She was in the database. The team reached out and set it up. (They call this “genie-ing” a date.)

Pascaretta and the gorgeous journalist met for dinner at Arte, an Italian restaurant with white tablecloths and a lush floral facade near Washington Square Park. The date lasted four hours. He paid for an Uber to take her to her apartment uptown, texting: “Hope you made it home OK” at 11:50.

“Made it home OK, thank you for a lovely evening,” she replied.

Not long after, she gave feedback to Avgitidis and the team: She wasn’t feeling any spark.

Pascaretta — crestfallen, but still smitten — tried once more, hoping maybe she’d just been put off by the formal atmosphere of the date, or by the oddity of having a matchmaker orchestrate it.

“Officially decided formal matchmaker dinners are a terrible way to measure romantic chemistry, even my favorite Arte,” he texted her. “Let’s go to the Knicks game 6/10 and I’ll put my theory to the test, although I can’t promise courtside with Taylor and Travis.”

She responded: “Thanks so much for the gesture, but I want to be honest. I’m not interested in pursuing anything romantically. Wishing you the best.”

For weeks after, Pascaretta turned it over in his head and during his check-ins with the team — regularly bringing the conversation back to “the journalist,” as he called her, or “the famous reporter.”

“I’m going to find a way to lobotomize you, Joe,” Avgitidis chided when he brought her up again during their latest Zoom call while she was in Greece.

It hung there between them: the unavoidable reality that you can spend thousands of dollars to insulate yourself from many of the pains of modern dating, but that no amount of money can help if the person you really like simply does not like you back.

Avgitidis leaned in close to her camera, her chin propped on her hands like a friend utterly absorbed. She tried to refocus him.

Was he certain there wasn’t any spark on this latest date to Dear Irving? The one with the petite brunette he claimed had felt more like a work interview? They stayed out for three hours, after all. “If someone’s not having a good time, they’re not staying past 40 minutes,” Avgitidis offered hopefully.

“I did send a note,” Pascaretta said, scrolling through his text messages: “‘Had a nice time, very nice to meet you,’” he read. “She goes: ‘You too.’”

Avgitidis winced ever so briefly, and then nodded: There would be no second date.

She pivoted once more, reminding Pascaretta of two more prospects: an Italian woman from the database whom the team seemed excited about (Pascaretta, perhaps less so) and a matchmaker whose profile he had stumbled across on LinkedIn. Avgitidis knew the woman professionally and had immediately called to see if she was open to meeting.

“But, wait!” Pascaretta said, adding: “There were other prospects. Not to keep building the pipeline here, but that’s what we do in software.” He wanted to know what the sisters thought about approaching his dentist, whom he finds so pretty and charming, he got Invisalign he definitely doesn’t need, he admitted.

“There’s some vibe,” he said. “I don’t know what the vibe is, but there’s a vibe.” What should he do?