A Grown-Up’s Guide to Online Dating
I dove back into the online dating pool recently, having ended an LTR (for those fortunate enough to be oblivious to dating lingo, LTR stands for “long-term relationship”), the second one I’ve been in since my husband passed away from cancer 11 years ago.
Given my two lengthy relationships, you might say I’ve had success with online dating, or—given that both have ended—you might not. I wasn’t so sure about that myself. So this time around, before I dipped my toe back in, I consulted dating coaches for their smartest strategies on swiping for women like me: the other side of 40 (make that 50), no time for nonsense, looking for hetero love in what I hope are all the right places (Bumble, Hinge, Match…). I had questions—and some of their answers surprised me.
Whether you’re a dating-app virgin (so to speak) or have been around the block a few times (ditto), these lessons will set you up for success.
Don’t swipe until you do this
Here’s the crucial first step I’ve skipped in my online-dating adventures, the thing that should happen before you even download an app: Define what you’re looking for. Duh, right? I thought I knew: a life partner who is kind, smart, funny, attractive. But that’s not nearly specific enough, says dating coach Amie Leadingham, who works with groups and private clients using a technique she calls “conscious dating.”
“Conscious dating is about really knowing yourself, being intentional,” she says. “It’s like creating a job description. You’re fleshing out your needs, your requirements, the things that matter to you in a relationship. And then screening people intentionally against those.”
Insert “mind blown” emoji here.
Because online dating can feel anything but intentional. Swiping mindlessly is easy; it feels like a game. But without a strategy, you’re never going to win. The first time I went on an app, I naively assumed that brilliant, creative, handsome men—or least ones with a command of grade-school grammar—would be the ones to like and message me. Nope. (Leadingham advises adjusting your expectations, that about 10 percent of the pool will be people who might be right for any of us.) I figured out that I needed to message people myself—which gets really discouraging when they don’t respond (spoiler alert: most don’t). Plenty of women just give up at that point, figuring the system doesn’t work.
But being intentional—adopting that screening mindset—is a game changer. It gives you more control; a good thing, given that online dating can feel maddeningly out of your control. And, perhaps counterintuitively, it makes the early stages of the process less personal, less emotional. He’s cute but on the opposite end of the political spectrum? He didn’t message back? He lied about his age or job? No biggie—he’s just not for me. Next!
You’ve got a job to fill, and someone will be damn lucky to land that position. Time to start recruiting.
Fine-tune those “job” requirements
Here are the kinds of deeper qualities that might make your list of nonnegotiables: someone looking for a serious relationship who is emotionally available, monogamous, financially stable, family-oriented, ambitious, adventurous, open-minded, politically aligned with you, respectful of boundaries—to name a few (and Leadingham suggests coming up with 10 to 15). Get really specific, since your definition of “spiritual” might not include organized religion, for example. Also, try to “focus on the things you want versus what you don't want,” she says, “because that helps you screen from a place of abundance.”
Another bit of pro advice: Skip the superficial, like height.
“Height is the thing that makes my job harder than any other,” says Tennesha Wood, dating coach and founder of The Broom List, a matchmaking service for marriage-minded successful Black singles. “I would say eight out of 10 times, a woman names height as one of her top three things. And I’m like, I don’t see the benefit in that for you or your relationship or your family or your future.”
Put real thought into your profile
“But don’t people just look at the pictures?” I asked the coaches. “Does the profile really matter?” The answer: a definitive yes, it matters.
Furthering the job metaphor, your profile is like your résumé or LinkedIn profile: It allows you to show who you are and explain what you’re looking to attract—people who are serious and intentional, just like you. They will pay attention to what you’re putting out there and take the cues in your profile as opportunities to engage, not just send the generic “Hey, what’s up” or “Hi, beautiful.”
(A note on these throwaway messages: I don’t know why people send them—maybe they’re lazy, just testing the waters, or haven’t read any articles like this one. But before you just delete, take a look at their profile; if it has potential, you can reply and try to get a convo started. Maybe they’ll rise to the occasion. See tips on engaging below.)
About the pictures: They aren’t the only things that count, but they sure do count. A lot. They should be recent, particularly your primary shot, the one that pops up when people are swiping. Then, ”make sure it's a good-quality photo,” says Wood. “Clear, well lit. No hats or sunglasses. You’re smiling, looking like a someone people would want to meet.” (That should all go without saying, but honestly, you’d be surprised.) “Another common thing I see is several people in profile pictures,” she says. “Nobody is going to take the time to figure out which one you are.”
In addition to a headshot, coaches generally advise posting a full-body shot (yes, like it or not, people want to see you head-to-toe) and a few others that show not just what you look like but who you are. Maybe you’re cheering on a favorite team, hiking with your dog, in a museum, or on vacation in a favorite place. “I should be able to look at your profile and say, ‘This person seems very chill, and they enjoy nature,’ or ‘This person is very outgoing; they love traveling,’” Wood says.
Next up: your written profile. Some apps offer prompts to fill in (I’m a real nerd about ________. My real-life superpower is _________), and most give you room for a paragraph or two. Either way, don’t think of this as a homework assignment you’d rather skip—it’s valuable real estate. Paint a picture of what it’s like to spend time with you. For example, on weekend mornings, do you like to go to the farmers’ market, a boozy brunch, on a long bike ride, or straight to your sofa to binge a show? Wood suggests finishing up with what you want: “I’m looking for a confident, outgoing, trustworthy man.” That way, she says, “somebody reads it and says, ‘Wow, that’s really me.’ Or ‘That's not me at all.’”
And don’t tell your whole life story: The point is to interest people so they want to know more.
Engage with intention
When you see a profile that appeals to you—someone who is attractive enough* and meets some of your criteria—send a message that sparks conversation and shows you took the time to read their profile. “I noticed you were in Spain—did you get to Barcelona? It’s one of my favorite cities.” Look for similar effort from people who message you. From there, see if there’s an easy back-and-forth between the two of you.
Respond promptly to messages—you might devote 30 minutes or an hour in the morning and/or evening to swiping and messaging. Have conversations going with a few people, if possible (time-efficient and helps you hone your dating chitchat skills). After three or four days of messaging with someone you’re vibing with, it’s time to talk, Zoom, or meet in person.
* I can’t tell you what this means for you. Of course physical attractiveness is a factor, but please, try to be open-minded. Remember: Attraction can grow if all the other factors are there.
Go forth and get vulnerable
You read that right. After three or four days of messaging, suggest meeting—that’s what both Leadingham and Wood recommend, and having been there, and done that, I agree. It’s easy to fall into a texting routine that can end up being a waste of your time, energy, and emotions. (You’ll see profiles that say, “Not looking for a pen pal” for that very reason.)
Whether you want to talk on the phone or do a video call beforehand is a personal decision. Some like this additional screening step; others don’t. I’ve done both and think it’s useful if you’re on the fence about whether you want to meet up. Regardless: “The goal is to actually get in front of this person,” says Wood. Etiquette-wise, either of you can take the step to make it happen. You might say, “Seems like we have a lot to talk about. Want to meet over a coffee?”
There are lots of opinions about that first IRL rendezvous. Leadingham thinks of it a “meet-up” rather than a date, and suggests coffee or a happy hour, for 30 minutes to an hour, max. Even if you’re having a good time, leave wanting more. Wood thinks segueing from a drink to dinner is just fine if the conversation and chemistry are there.
When you’re on your first few first dates, you’re going to be nervous—I mean, really nervous—which can make it hard to figure out if there’s a connection (he’ll likely be nervous, too, and perhaps not his best self). If you’re unsure, go on a second date; if you feel something after that and find yourself wanting to know about this person, go on a third, says Leadingham.
It may not be easy, but getting vulnerable is good. You might offer up that you’re working on your fear of flying, which holds you back from traveling, or that you had a tough upbringing and have been through therapy to come to terms with that. “Watch how the person holds space for you,” says Leadingham. Somebody who is right for you may say, ‘That's so awesome; good for you for working on that.’” (Mr. Wrong might become uncomfortable or judgy.) “And then they may start opening up and being vulnerable about their own challenges,” she says. If that happens, ka-ching! You can go ahead and check off “emotionally available.”
Test-drive a few cars at once
The pros suggest doing all of the above—messaging, meeting, and going on dates—with up to three people at once. I’ve done the juggle and see the logic: the more people you meet, the more you learn about yourself and the faster you’ll find your someone. (In theory, anyway: I have one friend who estimates she’s gone on 700 first dates in the past 14 years. Happy ending: She and number 700 just moved in together.)
“I hate to compare it this way, but it’s like buying a car,” says Leadingham. “You’re not going to buy the first car you test-drive. There are all these different features. You're not going to have a fair comparison of what ‘good’ looks like unless you date multiple people.”
But it can be confusing! I was on the other end of that recently, when a guy referred to something he thought we had done together. “That must be someone else you met on Bumble,” I said, and he looked properly chagrined.
This summer, I did go on one or two dates with a few different people over a period of several weeks and managed to keep them straight. It was indeed a learning experience, but also time-consuming and a little emotionally taxing. For me, if I’m feeling a connection after a couple of dates—and one person very much fit that description—seeing other people doesn’t feel right. (So I sent the others texts along the lines of “I’ve really enjoyed getting to you know you, but I don’t see us moving forward romantically.”)
This goes against Leadingham’s “probationary period” of 90 days, during which time she encourages you to continue dating other people. I was incredulous. “Really? You see multiple people, sleep with multiple people, for three months?” I asked. No, she explained. You don’t sleep with anyone for three months—you’re just getting to know them.
Oh.
Her point is that it takes time to screen for all your nonnegotiables, to see some flaws and decide whether you can live with them. Be honest with everyone along the way. She suggests you say, “I’m really enjoying my time with you, and I’m looking for something long-term with the right person. And right now we’re still in the early stages, and I am dating you and other people, but I’m not having sex with any. I want to wait until I’m exclusive with someone, because once I become intimate, I become emotionally bonded.”
I get it, and I appreciate it, but I can’t imagine dating more than one person for that amount of time. Which goes to show that, as with most things in life, different approaches work for different people. That guy I’m dating (we’re on day 70-something now) said recently that online dating is basically interviewing someone to be a grandparent to your future grandchildren. Honestly, despite the above advice, doesn’t that kind of say it all?
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