The Grown Woman’s Guide to Online Dating

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Once upon a time, internet dating was a vaguely embarrassing pursuit. Who wanted to be one of those lonely hearts trolling the singles bars of cyberspace? These days, however, the New York Times Vows section—famous for its meet-cute stories of the blissfully betrothed—is full of couples who trumpet the love they found through Ok Cupid or Tinder. Today an estimated one-third of marrying couples in the U.S. met online, and as many as 15 percent of American adults have used dating sites or apps. (Even Martha Stewart, who in 2013 declared in her Match profile that she was looking for a “lover of animals, grandchildren, and the outdoors.” Martha, have you considered Raya, the private celebrity dating app?)

Locking eyes across a crowded room might make for a lovely song lyric, but when it comes to romantic potential, nothing rivals technology, according to Helen Fisher, PhD, a biological anthropologist, a senior research fellow at the Kinsey Institute, and chief scientific adviser to Match. “It’s more possible to find someone now than at probably any other time in history, particularly if you’re older. You don’t have to stand in a bar and wait for the right one to come along,” says Fisher. “And we’ve found that people looking for a sweetheart on the internet are more likely to have full-time employment and higher education and to be seeking a long-term partner. Online dating is the way to go—you just have to learn to work the system.”

 So take heart: Whether you’re a first-time player or a seasoned contestant who wants to up her game, our troubleshooting guide is here to help, with advice from both experts and survivors on how to search strategically, handle setbacks gracefully, maintain sanity, and enjoy the ride—with minimal agony and maximum ecstasy. Your eligible bachelor awaits!


How To…Get Better at Online Dating

For guidance, Style Features Director Holly Carter turned to a pro.

Seven years ago, I signed up for Match.com, but I never took it seriously. For me, online dating is like exercise: At the end of the day, it’s easier to watch TV. But at 44, I started to realize that if I want a companion before Social Security kicks in, I have to leave the couch. I needed a trainer, someone who could help me focus—only instead of getting defined abs, I’d get a mate (hopefully, with defined abs). Enter Damona Hoffman, dating coach and host of the Dates & Mates podcast, who promises rapid results if I just follow a few tough-love rules….

Treat it like it’s your job.

The first thing Hoffman tells me: “This takes time and attention. I want you to be on the site at least three hours a week.” Uh-oh. That’s three episodes of The Sinner.

Put style in your profile.

Kindly, Hoffman refrains from mocking my unassisted self-description: “I’m a loving person who likes trying new restaurants and a sweet treat before bed.” (I never realized how dirty that sounds.) She asks about my hobbies, how my coworkers would fill in the “most likely to” blank. She then revises my profile, noting that I love cooking vegetables I grow in my garden, that Dave Chappelle has my kind of humor, that “meeting new people excites me: I could spend half an hour talking to the cashiers at Trader Joe’s.”

Tip: Whenever I meet someone for the first time, I drop a pin and let a friend know where I am.

Three-quarters of the profile should be about me, and the other quarter about what I want in a mate, says Hoffman, who tells me to be specific here, too: The goal isn’t to attract everyone, it’s to find The One. We come up with “My ideal match is someone who loves family, has an opinion on current events, and can hold his own at a cocktail party on a Friday night, then chill with me on a lazy Saturday.” The final touch is a headline that sums up my approach to life, like a personal slogan. Hoffman suggests “Family. Kindness. Friends. Faith. That’s what I value most.” Hmm. I’m spiritual and go to church, but “faith” sounds heavy. I swap it for “fun.”

Work your angles.

Hoffman looks at my photos and nixes the corporate headshot and mirror selfie. “You want to look natural and inviting. Mirror selfies often give off an air of vanity.” She says the best profile shots feature the three Cs: color (vibrant shades, especially red, grab attention), context (pics that involve your hobbies, like travel or, say, clog dancing), and character (something quirky or funny, “like you in your Halloween costume”).

For the main photo, we do a close headshot where I’m smiling into the camera. For the others, we do one of me outside in a green dress, one where I’m wearing something sparkly, and another where I’m standing on an escalator. This doesn’t reveal much about me besides my aversion to stairs, but it’s a full body shot, which Hoffman recommends. Agreed—as a curvy girl, I want to avoid first-date surprises.

I skip quirky. I haven’t worn a Halloween costume since I went like a pack of grape Hubba Bubba in sixth grade.

Take charge.

One reason I’ve been passive about online dating: Most of the guys have been a little conservative for my taste. (When you’re a black woman in your 40s, why do all your matches look like George Jefferson?) Hoffman says the algorithm, like a boyfriend, can’t read my mind; I need to message and “like” guys I find appealing if I want to start seeing similar people in my results. Plus, being more active should bump my profile toward the top, so I’ll be more visible.

Tip: I try to appreciate the bad dates. The craziest nights are your best stories.

I should make my messages personal, advises Hoffman: “Comment on something in his profile and follow with a question.” Dutifully, I tell one bespectacled prospect, “I like melty ice cream, too. What’s your favorite flavor?” I have some interesting chats, but nothing leads anywhere. After a lengthy back-and-forth with a cute guy who asks why I’m still single (beats me!), I try a Hoffman move, writing, “That’s a story better told over a drink.” He suggests… chicken fingers. As in fast food? Is this a sex thing I don’t know about?

But then—success! Someone “likes” me and asks me out within three messages. He’s into photography and makes his own pasta—and he is an Adonis. We have a short phone call, as Hoffman recommends, to set something up. His voice is velvety, but I’m skeptical. That’s online dating: You meet the freakazoids and think, This is the worst. You find someone great and think, Am I going to be on the next episode of Catfish?

Don’t rush it.

On the day of the date, I meet him at a restaurant. (Hoffman wouldn’t approve; she said to make the first date a quick drink, one hour max, but when Hunkamania suggested dinner, I couldn’t resist.) He’s just as swoon worthy in person as his photos! I’m supposed to focus on how I feel, not on “the package”—but it’s hard when the package is so beautifully wrapped.

He’s sweet, too, talking about his grandma, and we follow dinner with drinks. By the time he drops me off at my door, I’ve exceeded my time limit by three hours and 32 minutes. It’s kind of like blowing a diet: You know what you’re supposed to do, but then you see dessert and will power goes out the window. I realize I got lucky, that this was the dating equivalent of finding a magical unicorn. Plenty of my friends do online dating like it’s an Olympic sport, and they’ve had the most romantic evenings of their lives with guys who then promptly vaporize into the earth’s atmosphere. But whatever happens, it feels good to be back in the game. I decide to message Mr. Chicken Fingers, knowing I shouldn’t put all my eggs in one basket.


How to…Increase Your Odds of Finding a Match

Meet 9 people. Our brains are best equipped to handle five to nine options—any more, and we go into cognitive overload. “At that point you just start looking for reasons to say no, like ‘Look at his ugly shoes,’” says Fisher. Pick nine, meet in person, then take a break while you get to know at least one.

Set 3 deal-breakers. “If there’s something you truly can’t tolerate—smoking, for instance—okay, but I give clients a limit,” says House.“Most people focus on wants: hot, funny. You find the right one when you focus on needs: communication, mutual respect.”

Give it 3 dates. “Even if you don’t feel ‘chemistry,’” says House. “Chemistry doesn’t last. The attraction is important, but if someone meets your needs, you may find the attraction follows.”

How to…Find the Best Dating Platform

If you seek: Wedded bliss

EHARMONY
Answer an in-depth survey based on 29 “dimensions of compatibility” (e.g., humor, physical energy, communication style), then get a new list of potential soul mates regularly—no searching required.

If you seek: Other grownups

MATCH
Don’t worry, someone here will get your pop culture references: 39 percent of Match users are in the 37–52 age group, and 27 percent are between 53 and 72.

If you seek: The hip crowd

OKCUPID
An entertaining questionnaire (“Do you believe in dinosaurs?”) and open options: Look for anything from a partner to a polyamorous paramour.

If you seek: The driver’s seat

BUMBLE
With this app, every night is ladies’ night: Swipe right on an attractive gentleman, and if he’s interested, it’s up to you to make the first move.

If you seek: Maximum efficiency

TINDER
The “swipe surge” feature, available in select cities, alerts you when the app is getting a lot of action, so you can get some, too.

If you seek: A date with destiny

HAPPN
This geolocation-based app shows you well-matched users who are close by; check your Timeline to find hot prospects who have recently crossed your path.

If you seek: A big pond

PLENTY OF FISH
Cast a really wide net on this free site with more than 150 million users; quiz lovers will dig the cheekily revealing questions about relationship needs and seduction styles.

By Holly Carter

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