The Divorced Mom's Guide to Online Dating
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The Divorced Mom's Guide to Online Dating

Three years after my marriage ended, I was finally ready to date again. But with two small kids and a demanding job, how would I find time to meet men? The solution seemed simple: Go online. The reality? Keep reading.

Giving it a Try

I live in a big city -- Washington, D.C. -- but the world I actually inhabit feels small, two linked microcosms of home and office. My ex-husband and I work at the same company, so meeting someone on the job is a long shot. At the end of my workday, I rush home to relieve the babysitter and take care of my two young children. I'm too old and too busy to hang out in bars, and I'm not about to take up golf, hunting, or skydiving just to meet a man. "Go online," says my divorced friend Amy, as though she's giving me a tip on where to find Tory Burch boots at a discount.

I'm conflicted. On one hand, I'll have plenty of company: Forty million Americans are looking for love online, and 17 percent of U.S. marriages last year originated there, according to research. Those have to be better odds than sitting on the couch watching the Disney Channel. On the other hand, I'll have to swallow my pride. Somehow, mating via computer feels like a last resort. Isn't it bad enough that Prince Charming Number One defected? Shouldn't my good sportsmanship be rewarded with the effortless appearance of Prince Charming 2.0?

Evidently not. So my impatience, Amy, and a bottle of good cabernet gang up on me, and I take the plunge. There's no shortage of dating sites. One of the largest, eHarmony, actively sets you up with people according to a scientific formula based on a member's core values. That sounds a bit too Big Brotherish for me. I settle on one of the other large sites,, largely because that's where Amy met her boyfriend, Bill. "Let's write your profile," she says. "Think of it as an infomercial for yourself." She pushes the keyboard toward me and tops off my wineglass.

I type in my basic stats and answer questions about interests, exercise habits, and favorite things. I decide to speak from the heart. "I'm riding my bike to work today, talking to you in my head," I write. "Here's my list of Top 10 things you should know about me." Over my shoulder, Amy reads aloud. "'One: Everyone meets for a reason, a season, or a lifetime. The fun is figuring out which.' Good! That shows you're spiritual." "And not desperate," I add. "A date can just be about having a good time." "'Two. Do you cook? I find that sexy. There's nothing better than having my children (5 and 7) tucked in their beds while I pour the wine and you play Grill Master.'" "In other words, dude, I've got two kids," I say. "And I'm not cooking you dinner."

We laugh. Amy reads on, ending with my grand finale. "'Ten. So here's the thing. This is my first foray into online dating. I've been single for three years, and the pain of my divorce has finally lifted. I'm a passionate person, not perfect by any means, but I have a Go Big or Go Home attitude about life. If you are still reading this, then...'" We set my criteria filters to eliminate men who live beyond a 15-mile radius of me, smoke, exceed my age (47) by more than 15 years, and are shorter than my 5-foot-10. I upload a head shot, three photos of me on trips with friends, and one with my dad. For security reasons, profiles use pseudonyms. "Melina means honey," I say. "How about Honeybee?" "Perfect," Amy says, hitting submit. "Let the games begin."

The next day I receive an e-mail from MultipleOMan. "Welcome to Match!" he says. "You're hot, but you're outta of my league, so I'm taking a pass." He's cute in his baseball cap. "You're e-mailing to reject me? And how can 'MultipleOMan' and 'out of my league' be in the same message?" I respond. We banter, make friends. And boy, do I need a friend. I'm clueless. Every day the site pairs me up with five people, and I'm supposed to indicate whether I'm interested. I can also search for men who fit my criteria and e-mail them or "wink" to test the waters. "MultipleOMan, how do I work this thing?" I ask. "Respond to matches of the day, wink, or what?" "Do nothing," he says. "Your in-box will fill up, I promise."

I'm skeptical, but he's right. Profiles steadily trickle in. A little becomes a lot -- perhaps because I'm the new kid on the block -- and within a week I get 1,000 clicks on my profile and 30 e-mails asking me out. Match sends a pop-up directing me to reset my filters more stringently. "You got the pop-up!" says Amy. "That's flattering." I feel like I've won the slots for men! What's interesting is that most mention my Top Ten list. "I feel like you're talking to me," writes one. "You make me smile," says another. And the "Do you cook" query turns out to be a surprisingly concrete conversation starter. Not only do several men offer to make me dinner, but their responses also tell me a lot about them.

Amy checks out the pickings. "Would you want to kiss him?" she says, pointing at a would-be date who's 15 years older than me. "You've got to vet according to what matters most to you." I ponder this for a moment. "I'm looking for a smart, funny, kissable dad around my age who lives nearby," I announce. Bam, bam, bam, just like that Amy deep cleans my virtual boyfriend closet. We reset my criteria so the guys have to be younger, taller and local. That leaves six. I set up dates with all of them for when I return from a two-week vacation in India.

But after I arrive in Mumbai, I discover to my horror that my Match mail has been sending my out-of-town auto-reply with my real identity. Yikes! This is unsafe, a real Match no-no. Several suitors jump in to help. LetsDance, an IT specialist, actually calls my office to sort it out. I decide he deserves a personal thank-you. In the meantime, instead of soaking up the sights of India, I'm searching for Wi-Fi to e-mail HorseDad. Over the course of 10 days I experience an entire relationship -- including flirting, deep talks, huge fight, and ugly breakup -- with a total stranger. I realize I may be getting a little addicted to the sudden new attention.

Real Date Dilemmas

My first in-the-flesh date is a quick drink with LetsDance, per MultipleOMan's suggestion to keep the initial encounter brief. When I turn from the bar to hand him his glass of wine, he says, "Hey! Be careful pointing those things at me!" He's referring to my breasts. Next. Ron627 is a handsome, preppy lawyer. My parents would approve. But we struggle for conversation. I've been out of the dating scene for so long I've forgotten how excruciating a bad date can be. Perfect on paper does not equal chemistry. "I'll be in touch," he says as we part. "That's the polite way of saying 'I'll never see you again,'" translates MultipleOMan. Ouch!

Over the next few months I have many pen pals and go on one-drink, one-hour dates two to three times a week. I slot them in like meetings between work and home -- the palate-cleansing sorbet course of potential romance between the two demanding worlds I navigate. It's fun! D.C. has a large pool of eligible men. I meet guys who work for the World Bank, the State Department, NASA, and the CIA (a national security expert who didn't know his own wife was cheating on him with their kid's hockey coach!). Everyone's nice, really. The good news for us 40-something women is that there are terrific men out there. Still, I've yet to accept a second date.

Then I hear from Uphill50. His e-mail is witty and self-deprecating and makes me laugh out loud. He's funny in person, too, though not my physical type. (I like big guys and Uphill50 and I could fit into the same jeans.) But as we get to know each other, I discover that we have fun doing not much, like sitting in front of the fire playing Wurdle on my iPad. Since our exes have custody every other weekend (he has a school-age son), spending time together is easy and discreet.

I'm not in love, but Uphill50 is kind and smart. We make it from Halloween to Valentine's Day. Then we put a deposit on a trip to Mexico, and I start to feel trapped. I know in my gut that Uphill50 is wrong for me. He's ready to retire and live frugally after a long career in academia. To be honest, that scenario is too quiet for my taste. Sorry, but I find ambition sexy. I try to explain this to him tactfully, but I hurt his feelings. He returns the favor by leaving a bag of my belongings on my porch.

So it's back to Match mail, which I've barely glanced at in months. Among my e-mails is one from Fishrman62, who has a Ph.D. in biology (smart), a sexy consultant job (ambitious, yay!), and a boat (fun). Plus he's 6-foot-4 and looks kissable. The following Saturday I meet him for the usual one drink, one hour. Fishrman62 is tall and handsome, and he has waited before ordering (sweet). Within minutes we discover that we grew up in the same area of New York state, lifeguarded at neighboring country clubs, and have mutual friends. Good thing the kids are with their dad, because our date ends at 3:30 a.m., and yes, Fishrman62 is kissable. He does raise one red flag: Despite his nine-year marriage, he says, he has never felt a sustained commitment to any one woman.

We date and date and date. His professed inability to commit does not sync with his behavior. Fishrman62 calls constantly, cooks me dinner, and describes our weekends together as "heaven." I introduce him to my friends, who give him an enthusiastic thumbs-up.

Then, a few months in, Fishrman62 starts to act aloof. One night, after a three-hour conversation on my front-porch swing, he kisses me good-bye, and I know. I never again want to be on the other end of a blank kiss like that. No woman should. "You don't feel connected to me, do you?" I ask. "I don't feel connected to myself," he mumbles. "I can't help you with that," I say. If my failed marriage taught me anything, it's that I can't change anyone but myself.

This one hurts: Fishrman62 had real potential. I dull the pain by plunging back into my in-box, where I find ActionMan. Over drinks I wonder if he's secretly the 4-Hour Workweek author Timothy Ferriss. He's an investment banker who has studied abroad, has four degrees, and is about to take his company public. I learn all about his seven siblings, his dyslexic son, the messy divorce from his cheating wife.

When he's not talking he's devouring me with his eyes. Unlike Fishrman62, he's not ambivalent in the least. He "loooooooves" my looks, my dress, the way I tell a story. Two nights later we go out for a seafood dinner followed by a nightcap at my place, where we talk late into the night. He mentions that he's house hunting. "Open houses are fun," I say. "Wanna come with me on Saturday?" he says. "You can meet my dog." My kids are with their dad, and ActionMan is a ball of fire. Why not? So two days later I buy dog treats, put on a red halter top and white jeans, and wait on my porch. I'm excited.

One o'clock comes and goes and no ActionMan, no dog, no...nothing. I text and call and don't hear back. Has he lost his phone? Is he dead? I check Match mail to see if he's contacted me there. He hasn't, but his profile tells me that ActionMan is seeing lots of action. Just not with me. I look at the dog treats. Too much, too fast. Sigh.

"It's a numbers game," Amy says when I tell her about my hot, heavy, evaporate experience. "Be patient." Instead, I decide to quit while I'm ahead. And I am, by a long shot. The 15,000 clicks on my profile have given me a confidence with men that I lacked even in my 20s. I've gone on 37 dates, had two semi-relationships, and flirted endlessly. I've also learned a valuable lesson about my unhealthy tendency to jump in too soon. I'm grateful to all the men who took me out, opened their lives, and treated me well. Collectively, the experience was like a defibrillator, shocking me out of my post-divorce funk and back to the land of the living.

But all this dating has taken a toll, leaving me exhausted and resentful that I no longer have time to do things I enjoy, like see my girlfriends, practice yoga -- or sleep. So I'm taking my newfound romantic optimism from the virtual world into the real one. My love life is back in the serendipitous hands of fate.

Signing off, Honeybee.

Originally published in Ladies' Home Journal, February 2013.