One night right before bed, Paula Bragg decided to break up once and for all—with online dating. It wasn’t OKCupid’s fault exactly. Nor’s. Nor Tinder’s. Bragg simply decided after a series of dead-wrong (yet often humorous) hangouts and exchanges—did you know men post pics of themselves wearing Chewbacca costumes and T-shirts reading “Show Me Your Kitties” on these charming sites?—she wanted to try a more traditional approach to meeting a man.

“After I deleted my profiles, I turned the light back on and wrote a post on Facebook,” explains Paula, 37, who serves as the director of philanthropy for Mt. Washington Pediatric Hospital. Here’s what it said:

In the quest to go on my #LastFirstDate, I’m off of online dating sites. Makes sense, right? LOL! Well, it does if you believe, like I do, that with all the friends I have—and all the friends you have—someone out there knows a great guy for me!”

Earlier that night, she’d been at a work-related event when a friend yanked her across the room to introduce her to a man who, according to her pal, “knows everyone.” A light bulb turned on! Her friends on Facebook (and their friends) really do, in a sense, know everybody in Smalltimore—and more importantly, many of them actually know Paula, in person. (That means they can vouch that she is, indeed, an attractive, intelligent, funny and sane human being seeking a long-term relationship.)

Paula’s ballsy Facebook post, dated Nov. 6, quickly received more than 200 “likes” and 12 shares. “Send me your overflow,” wrote one friend. Within less than two weeks, she received eight introductions and went out on two casual dates with men she wants to see again. 

“It’s been really fun putting the control in my friends’ hands,” says Paula. “I feel like I’m actually the one in control.”

Let’s have a heart-to-heart here, lovers. Who hasn’t yearned to play Control Freak Cupid now and then—or play God, as some realists might term it—and set up a good friend with a good-looking somebody or other?

Back in my 20s, this writer had easy luck urging a very shy and solitary roommate to call a man we’d run into at the supermarket. On a Post-it I scribbled, “Call Javi!” Over coffee cups, I shouted to myself, “Javi is gorgeous!” During a commercial, I whispered in her ear, “He might meet someone, like, tomorrow.” I wouldn’t stop till she turned tomato-red and picked up the phone, which I’d set in her lap. They’re now happily married.

But was my aggressive approach inappropriate? It’s not like I even knew for sure my roommate wanted to go out with the guy—I’d merely sensed chemistry in the canned soup aisle.

Dating coach Tammy Tilson, a licensed clinical social worker, says I was playing with fire back then, and lucky for all three of us nobody got burned (hey, it’s almost Valentine’s Day, hence several sizzling-red metaphors.) Singletons greatly need the sense of control and confidence that Paula describes owning if they’re going to play the dating game at the top of their emotional and intellectual game.

Tilson founded her Towson-based service, Upscale Dating, in 2013 because she’d encountered so many romantically anxious adults in her one-on-one therapy sessions—many of whom have faced innumerable disappointing online dates (sometimes dozens per month, according to my single friends), regular rejection and understandable exhaustion. She coaches these ladies and gents to get dating-ready, and empowers them to continue once they’ve begun—offering tips on everything from dating profiles to dinner conversation.

“The first important step is to ask somebody if they’d be interested in being set up,” Tilson says. “Sometimes single people feel ambushed. Don’t assume they’re not happy.”

Check. What’s next? Write your simple commands on a Post-it? Extol the virtues of your proposed candidate? Gently mock his drawbacks? Rattle the phone in her face? Not so much.

“Give your friends some basic information,” Tilson explains. “Show them a picture. You have to be honest about the person, but don’t get into anything too personal or tell their life story. Don’t say, ‘She’s slow to commit’ or ‘He’s sweet but a chronically messy kisser!’ Subjective information can sabotage. Just share their ages and if they’ve been married, have kids, etc. Leave it to a minimum.”

Tilson grants this advice may be easier said than done among close friends, but it’s a nice humane guideline to keep in mind. I asked her why so many of us are drawn to make a match.

“I don’t know if we’re projecting our own needs or being romantic,” Tilson says. “‘I’m happy; you be happy.’ Or: ‘Everybody’s married.’ Projecting wishes, desires, goals. I think people like to help people. They think it’s fun. But they don’t always think it through.”
Saralyn Lyons, bar manager at the Lyric, admits she definitely did not think it through when she set up her two Japanese steakhouse co-workers, Colin and Fran.

“Fran and I had a history of liking the same guy,” Saralyn, 25, explains. “‘You should ask out Fran,’ I told Colin, and he did. They started going out. At first, I felt proud. But one of the first times they hung out without my facilitating it, I realized I didn’t want this to happen—I became possessive of Colin. I was horrible! Whenever Fran would talk about their last date, I’d say, ‘Awwww! We used to do that.’”

Even though the young waitress asked each party if they were interested, she failed to understand her own under-the-radar crush. After Colin’s relationship with Fran ended on its own, he and Saralyn soon hooked up—they currently live together. Saralyn hasn’t spoken to her former friend Fran since the young woman quite rightly called her out on being jealous of her budding romance.

Tilson says it’s also important to be sure to consider life stages and personal preferences before you strike your match (heat metaphor). Be realistic. Be practical.

“If you know a guy is a workout maniac, don’t set him up with someone who doesn’t care about the gym,” she adds. “If you know a girl wants a baby, and you know a guy with three grown kids, he’s probably done with that.”

Might sound like a no-brainer, but not everyone takes time to compare these important qualifiers. Love is a much more fickle thing than just “he’s nice” and “she’s nice” and “they’re both single.” Bingo!

Speaking of fickle, I have one intellectual male friend who says he’d be open to a setup in a second. Not so fast. He wants a slim brunette with big boobs, who speaks a minimum of two languages and…the list goes on. In fact, I know one, but she’s not single right now, and if she were, I’m not sure I’d go there.

Tilson agrees: “If your single friend is very restrictive, just don’t set them up.”

Which brings up another key tip: Matchmakers must handle their friendships with tender loving care, especially if they know both the dating friends well.

“You can jeopardize your own bond by getting too involved; you could break trust,” says Tilson. “If the woman says ‘I didn’t like his body,’ don’t pass that on! Don’t invite the comment. Be as diplomatic as you can. Boundaries protect everyone’s feelings.”
Jennifer Ciattei, a 55-year-old web content writer, stepped super-duper carefully when she put together two quiet, creative types, both close friends of hers, but near strangers to each other.

“I love this female friend—and she deserved to be happy,” Jennifer says. “The male in the equation is the nicest guy in Baltimore—and a talented musician. But you just never know. It was important not to get anybody’s hopes up. Especially when you’re not kids. People might be a little more gun-shy than if they’re younger. I suggested coffee. He took a long time to get back in touch with her, but I didn’t weigh in. Now they’re getting married.”

Tilson, 47, is herself divorced with two kids. But she’s seriously involved with a man who was a friend’s pick for her. (“Her boyfriend is best friends with my boyfriend,” she says.)

So what’s the secret ingredient? How did her friend know she was making a brilliant match? She didn’t, of course. Chemistry may be a science, but not when it comes to dating.

Tilson says she and her now boyfriend simply approached the first date with open minds—neither assuming they were walking in to meet their future spouse nor predicting “I’m going to die alone” doom and gloom. (That’s a lot for a complete stranger to overcome over a cocktail and a plate of fried calamari.)

“Try not to have preconceived notions, if you can help it,” she says. “You can’t forecast what will happen. But if you don’t go, you’ll never know.”

On a personal endnote, I think it’s all well and good to aim to be open as a dater, but I also know you can’t force it. When I met my husband—six years ago through a strategic friend, at her office Christmas party—frankly, I was at a closed-shut point. For months I remained so. That night at the office party, my intended love match was wearing the worst overcoat: Remember Steve Winwood in those super shoulder pads? And he had long, salt-and-pepper hair, like an REO Speedwagon fan at a reunion show. I simply wasn’t interested.

When I met him again randomly, months later at a literary reading, he wore faded jeans—I noticed he had nice eyes. We sat together and chatted easily. In my more open mood, I realized my friend had been exactly right: This guy was smart, empathetic, funny…and gorgeous (especially so minus the rocker hair I later persuaded him to trim). Thank goodness my friend Ditty knew we might make a perfect pair, because a dating site would never have linked us, based on age difference, and the fact that Michael would never have set foot on such a site to begin with.

My advice to singleton daters: Trust your matchmaker friends, invite their assistance and thank them. To those making the potential match: Tread carefully when introducing people; operate as your most generous self—and if your heart’s in the right place, don’t be afraid to play Cupid.

Cupid Case Studies: Fix-up hits & Misses

When I was about 37, a friend at work asked if I’d like to be set up with a silver fox. I told my friend sure I would meet him. Soon my phone rang. When I answered, the gentleman said he was the best-looking man in town and would I meet him for a drink that afternoon? I said OK, warily. Over drinks, he mentioned, ‘Your breasts are beautiful!’ I was so freaked out by this guy that I started babbling, ‘They are not! I have had surgery from a lumpectomy!’ To which he replied, ‘Well, I have a little birth defect, no worries,’ and then proceeded to open his shirt and show me his THIRD NIPPLE. I literally ran out of the bar. –Claire, 50

Frog Prince
A former colleague introduced me by email to the man of my dreams—or so I thought. He was divorced with two small, adorable kids. I was ready to play “hot stepmom” and marry this guy, who was an executive in D.C. with similar interests and background. But in the first five minutes after we met, I wished I’d requested the fake “your house is on fire” emergency call. He had the voice of a frog, moved like a robot—and, in the middle of the restaurant, loudly recounted numerous therapy sessions with his ex-wife. Worse: he kept trying to kiss me. Turns out, my friend had never met the guy in person… only on Facebook! People can be very different in 3D. –Jessica, 41

Trick or Treat
I was 27. It was Halloween, and my friend said, ‘I know this Baltimore artist who makes masks.’ We went to her house. There were masks everywhere! She was a very interesting person. I liked her. But I could sense she was a private person. A couple months go by. I’m in a meeting for work, and the phone rings. A mutual friend’s on the line: ‘The artist wants you to ask her out.’ So I did. I picked her up in a car that was completely screwed up—you had to put your foot on the door to yank it open. She didn’t mind. We’ve been married for many years. –Anonymous, 60

Cat People

Rick understood it was a setup. Our mutual friend David had known Rick’s last girlfriend and wanted to see him partnered up—but I didn’t know a thing. After our group dinner, Rick drove me home, and I was thinking: I really like this guy. A week later I asked David for Rick’s number. (Eventually I learned he had considered other female friends for Rick, but decided they didn’t fit the part.) When I called, Rick didn’t sound wholly enthused. But then I borrowed his cat carrier, to transport a cat I’d adopted the same day he and I met. Afterward, we went on an amusingly error-ridden​ dinner date: They brought us the check before the food arrived. We’ve been together 22 years, married for 16. –Elisabeth, 45

Fix Me Up!

Tips for singles who want their friends to play Cupid.

Just Ask. If your five BFFs knew the man of your dreams, they would have already introduced you. Consider directly asking other friends you trust and admire if they know interesting people in their social circles who are single and ready to mingle.

Divide & Conquer. So you met an adorable woman who wasn’t quite for you? Introduce her to another single friend. (Online daters call this “recycling”—like a pre-screening service to increase odds of finding “The One.”)

Do Dinner. “Millionaire Matchmaker” Patti Stanger says first-time daters need to go out one-on-one with an element of flair and formality. “Drinks are an audition, coffee is cheap and lunch is an interview—dinner is romance.”

Play Host. In lieu of sulking (or stalking your ex) on Valentine’s Day, host a singles party where everyone brings an eligible person of the opposite sex. But, be careful, bringing your secret crush usually backfires.

Partner Up. Ask your married friends to host a “Third Wheel” happy hour or dinner party. That’s when each couple brings their favorite singleton (the one who tags along on all their dates) in hopes of coupling them up.

Be Positive. Not everyone is great at matchmaking. (So you really think I want to date your 74-year-old, thrice-divorced Uncle Morty?) Try not to be offended if your friend suggests a “no, thank you” suitor. And if a fix-up goes awry, always find something positive to say about the other person, such as “He had excellent taste in wine.” (No need to mention: “Unfortunately, he drank too much of it and started crying at the table.”)

Ditch the iPhone. Do not text your friend (or anyone else) the blow-by-blow during your date—if it works out, you’ll want some privacy. And either way, your date deserves your full attention.

Nice Touch. The very next day after, call or email your friend to express your gratitude for the fix-up. Whether your pal ignited a love/lust spark or put the “blind” into blind date, most matchmakers have great intentions—and, with a little practice and kind feedback, their Cupid’s aim might just improve. –Jessica Bizik

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