What’s the Single Life Like in Westchester?

A look at dating and the singles scene through the eyes of seven county residents.

We take an in-depth look at the dating and singles scenes in Westchester through the eyes of seven eligible county residents.

Living the single life is synonymous with urban living, but plenty of would-be lovebirds roost in Westchester, too. In fact, according to a 2016 census report, nearly half of the county’s 974,542 inhabitants are single, meaning a lot of people from Mount Kisco to Mount Vernon are looking for that special someone. And it’s not just 20-something college grads, either: One-third of the participants in this story are either divorced or widowed residents in their 50s or older. So, what is it like to be single in the suburbs? We asked some of our county’s eligible singles, who enthusiastically shared their experiences and tips on dating in Westchester.

Who’s Looking for Love in Westchester?

Like many singles we spoke with, “dating has become a large topic in my life,” says self-proclaimed “Miss White Plains” Mary Kelly, a 37-year-old executive at Heineken USA’s White Plains headquarters. “I’m clear on the kind of man I want in my life and less open to games and nonsense,” says Kelly.  Sixty-seven-year-old New Rochelle divorcée and retired executive headhunter Estelle Newman agrees, saying she applies the same attention to detail to finding a boyfriend that she did when hunting for that next great CEO. “I define romance as the chemistry or connection that can cause a mild-to-extreme case of butterflies,” she explains. Yet, “Some people in their 60s just want companionship.” Newman carefully vets potential suitors, usually through friends or a dating website, to ensure that once they meet, there’s a better chance of a successful date.

Thirty-eight-year-old Jamaican-born Semone (she asked that we not use her surname) says that finding single people her age is tricky because, “Most of the men in their 30s are either in committed relationships or aren’t looking for anything serious.”

Most of our respondents were open to dating divorced people, but are cautious about remaining baggage from previous marriages. “Don’t gush about your ex unless you want the date to end right away,” suggests 55-year-old James Reichert of Bedford. Still, it’s important to be up-front about your marital status. No one wants to end up with someone who is not officially unattached but covertly on the hunt. Reichert says he steers clear of these “dangerous liaisons.”

Yet, the recently divorced father of two says he’s dated women in every age group from their 20s through their 60s, and each has brought its own set of pros and cons. “I dated a 27-year-old who was more mature than many 50-somethings I’ve met,” Reichert says. But that relationship ended because they had limited mutual interests.

The Westchester Dating Pool: Ocean or Pond?

John Garcia, aka HOT97’s DJ Juanyto, thinks: “Westchester is great for meeting people — it’s very diverse.” The 36-year-old New Rochelle native’s day job as a DJ means he often interacts with many of the county’s crowd when he’s spinning at local hotspots like Scarsdale’s 808 Social. Still, when it comes to dating one-on-one, “I prefer places without all the crowds, so I can enjoy a conversation in peace,” he says.

Westchester singles seem to prefer romantic partners who also live in the county. “Even though White Plains is just a 35-minute train ride to the city, I find that people in New York City don’t want to date people in Westchester and vice versa,” says Kelly. “I lived and/or worked in Manhattan for 12 years, and now I would much prefer to date someone in Westchester. Logistically, it’s easier.”


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“I find that dating as an LGBTQ woman in Westchester is pretty hard,” says 28-year-old White Plains resident Mallory Cruz. “And it’s even harder as a woman — most cities with gay bars and clubs cater to gay men. Though there used to be a gay bar in Westchester, it’s gone now. Add the fact that the LGBTQ community is small here, and dating is challenging because there’s just not that many people to date.”

Once You Find a Date, Where Do You Go?

Semone suggests thinking outside the box to find the best first-date spot. “I’m interested in anything from action movies to spa dates,” she says.  “I love day dates, too — who says a date has to be under cover of darkness?” Plus, a day date means you can still hit the town in the evening — with someone else — if your day date goes sour.

Eastchester resident Sally Veltidi, a 39-year-old superintendent of parks and recreation, says Westchester offers all sorts of excellent spots for a first date. “It seems like a restaurant opens every week around here, so there’s always going to be something new to try.”

Reichert and Newman prefer active first dates, like a brisk walk in the park. “Coffee is a ‘non-date’ date to me,” says Newman. “I like meeting dates in Manor Park in Larchmont. It’s a great venue for walking, scenery, and it’s close enough to town so that, if things are going well, you can go grab a bite to eat.” Reichert also likes to walk on a date because, “Coffee turns into more of an interview.” Movement also alleviates some of the first-date jitters.

“I love White Plains because you can go to the City Center and watch a movie or dine in one of the many restaurants on Mamaroneck Avenue,” adds Cruz.

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Love in the Digital Age

Okay, so how do Westchester residents find their dates? Mimicking national trends, most have an online dating profile. Many singles maintain multiple profiles on various sites and apps, depending on what they’re craving. (See Love In The Digital Age, page 85, for a breakdown.) For the most part, however, Match.com and eHarmony.com seem to be the most popular social-matchmaking sites for people looking for more than a one-night stand. Still, meeting through a mutual acquaintance, either online or IRL (in real life), is the preferred method across the board.

Reichert says that the sheer quantity of potential dates in Westchester on social media apps vastly outnumbers what he’s seen in other parts of the country. “New Yorkers are slightly more impatient than Midwesterners (where I am from), but there’s simply so many more here — an online search in my hometown of Cincinnati might result in 16 matches, but here in Westchester, I’ll get 1,000 possible matches,” he explains. So, how do you decide who makes it to the next round? “Do your homework,” Reichert recommends. “Some people tell stories that are just too good to be true, and after a couple of emails, it’s pretty clear who’s trying to pull your leg and who’s legitimately looking for a date.”

A few of our singles tried the digital route and decided it’s not right for them. After going to the old online standbys like Match, OKCupid, and Hinge, Kelly unplugged her dating life. “I know tons of people who had success with social-media dating apps, but they’re not for me. I’ve found that people misrepresent themselves. When you meet someone in person you can typically tell within minutes if this is someone you want to get to know better,” she says. DJ Juanyto never bothered to create an online dating profile, preferring to make real-life connections through mutual friends.

“I use OKCupid more than Tinder, simply because conversations on Tinder tend to fizzle,” says Cruz, even though she finds more women who match with her Tinder profile. On either app, she says that people are upfront about whether they’re on the market for a relationship or a tryst.

Love in the Digital Age

A Guide to Dating Apps

Match.com, eHarmony

  • Good for finding people interested in long-term relationships.
  • Both require a lengthy application process.
  • Match offers the opportunity to block cellphone numbers and other identifiers to discourage unwanted advances.


  • Free; features short, member-generated quizzes and even options for those seeking polyamorous relationships.
  • Doesn’t let you see who’s looking at your profile.

Coffee Meets Bagel

  • Free basic membership
  • Female-centric (women have more control over conversations/meetings)
  • Premium membership pricy at $35/month

Plenty of Fish, Tinder, Grindr

  • Geared toward casual hookups and one-nighters.

All our participants urge total honesty about who you are and what you want out of a relationship. “I was supposed to meet a woman for coffee. She told me she was a fortysomething former model,” recounts Reichert. “Her profile picture backed up that claim, but when she showed up, it was immediately clear that she had not been truthful. I paid for my drink, got up, and excused myself, saying I couldn’t go further.” Unfortunately, it didn’t end there. “She started calling me, leaving me nasty text messages, and saying I was a horrible person for wasting her time,” Reichert says. “I called her back and told her that since she hadn’t been honest with me, there was no way we would ever establish any kind of trusting relationship.”

Honesty, for Reichert, extends to getting physical as well. He says he has no qualms about asking for medical reports as a precaution against STDs. “I require all potential partners to show me proof that they do not have sexually transmitted diseases,” he says.

The singles we spoke with agreed that being upfront about their intentions is important, even if the conversation can get uncomfortable. “Once upon a time it would have been completely unacceptable to talk about your intentions, but I think it’s great when everyone is clear and honest,” says Kelly. Misrepresenting who you are is almost a running joke when it comes to vetting online profiles. “Represent yourself truthfully,” says Diana Mandell, New York City-based relationship coach and author of The Attraction Method. “People tell me it’s incredibly frustrating when someone’s online life doesn’t match up with reality.”

Texting — The End of Good Conversation?

Texting is part of the modern Westchester dating scene, for better or worse, even though nearly everyone expressed the importance of being able to converse in real life. “I feel like I barely talk on the phone anymore,” Veltidi says. “But if I’m interested in someone [based on their profile] then I call and talk.” Kelly laments the influence of technology on dating. “I believe the art of conversation is dying. I’m reminded of that every time I’m at the gym or at a restaurant or bar. I’m outgoing and often make small talk with men and find that most of them don’t know how to respond.”

Meanwhile, Newman has wholly embraced texting: “I love it! Sometimes that little note during a work day brings a smile without the time an email or phone call requires.” Cruz also finds texting beneficial. “I find I can express myself better in text than over the phone, and I text to ask people out that I meet through dating apps.” Still, Semone says texters need to be careful before hitting send: “If you don’t know someone, subtleties like sarcasm and frustration do not come through in a text.”

ISO: A Good Time or A Long-Term Relationship?

Across the board, it appears that singles in Westchester are looking for romantic partners who are willing to try new things, go to new places, and are honest about their expectations. For Semone, “Intelligence is a must.” That doesn’t mean only PhDs need apply, however. “Social intelligence is just as important as being book smart,” she says. “It’s all about having confidence in yourself.”

Cruz says she’s looking for a woman who she can be friends with even if there turns out to be zero romantic connection. “I’m autistic, and I’m looking for someone who’s very open-minded about that, as well as someone I can laugh with and be honest with about who I am.”

As for signs a date went well, our singles point to rapid follow-ups via text message or online, with a request for a second date. Is there a magic number of days to wait before calling for date No. 2? “If they’re in their 60s or 70s, what are they waiting for?” quips Newman. Semone says you know right away when you’re ready for that second date, “because you don’t want that first date to end! Then there’s no need to wait a couple days before asking someone out again.”

Mandell suggests being realistic about what to expect on a date. “Without being too pessimistic, don’t set your expectations too high. If you have a bad date, grab some comfort food and get back out there. You can’t let a bad date discourage you.”

Sometimes, finding the right person takes a little luck. “There is passion, sex, fun, enjoyment, and friendship within all of us,” says Newman. “Dating is an adventure.”

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