04/30/2012 09:35 am ET Updated Jun 30, 2012

Matchmaker, Don't Make Me A Match

I am obsessed with matchmaking. With Americans becoming brides at age 29 and grooms at 30, I, also 30, boast a teeming pool of single friends, friends of friends, and friends of friends of friends -- with acquaintances thrown in when times are tight -- from which to mastermind introductions. I produce thoughtful and educated pairings, humming Mendelssohn's Wedding March as I middle-man contact information for two people I am confident will click.

To date, I'm zero for four.

I had pure intentions when I made my ascent into matchmaking five years ago. I felt, as the engaged one of my group, that it was my karmic duty to find mates for those around me. It didn't matter that no one was asking me to play cupid. I embraced my self-appointed role with the gusto I usually reserved for a) finding new restaurants, b) eating at new restaurants and c) complaining about what's wrong with new restaurants, and began paying creepy-close attention to my friends' love lives.

Over our usual half-caf mocha latte Wednesday date a week later, my friend Chloe announced she had broken up with her boyfriend. He was straight-up too boring, she decided. She, the table dancer at every party, wanted someone more fun. My old neighbor Mike fit the bill. In addition to being the most fun person I know, he's also smart and cute and makes a disgusting amount of money. Sure, there's the small issue that he works as a stripper, but I was positive Chloe could look past his evening activities. Though she was still raw from her breakup, I insisted they meet.

Chloe went out with Mike three times (only three times!) before deciding that she couldn't handle a mate who paid for dinner in singles and declared him a no-way-not-now-not-ever kind of guy. I complained about her selfishness to our mutual friend Samantha before the obvious solution emerged: I would set Samantha up with someone to offset the damage I'd done to the Universe's balance. I took her reluctance as shy appreciation and lunged back into my mental stockpile, crunching faces until I landed on my former classmate Chris. A singer-songwriter, Chris was into the same creative, artsy scene in which Samantha flourished. I was positive they'd meet, spend hours discussing literature and art and old 80s sitcoms (how can a shared appreciation for "Perfect Strangers" not bond people for life?) and move in together by week's end. Cue to real life: Samantha, a competitive runner, noted how out of shape Chris was. Chris, a competitive eater (okay, maybe that's a stretch, but ... ) hated that Samantha only ordered a salad at brunch. They considered their one date one too many.

By this point, I was consumed with my own wedding planning. There was, however, just enough available brain space for a pattern to emerge in my maybe-not-thinking-clearly head: If preparation wouldn't work, I'd have to rely on dumb luck. Whoever was in the same place at the same time got my blessing. To that end, I tried to force a spark at my wedding between my younger sister, Lisa (the maid of honor), and my soon-to-be husband's friend Matt (the best man). I foresaw them falling in love instantly, mouthing the vows with us as they held hands across the aisle. What actually went down was a fight over who gave the better speech.

They were under too much pressure, I decided. I need a carefree dumb-luck couple. And I chose my friend Natalie to test it out.

"Look on my Facebook page," I told her. "Pick any guy you want, and if he's single, he's yours." She chose my old roommate Bobby. He was single. And I set out to make him hers. But Bobby's insistent claims that he was maybe, kinda, sorta going to get back together with his ex -- a woman he hadn't seen or spoken to in six years -- made me a bona fide liar. My matchmaking track record had dwindled from three dates to one date to one forced interaction to ... what? This? A refusal even to meet? I waved the white end of my favorite scarf.

"You're trying too hard," my husband, John, told me as I brooded over my sesame chicken that night. "Do these people even want to be set up? Or are you telling them that they want to be set up?"

He had a point. I had envisioned a built-in support group on my personal trajectory, my daydreams expanding beyond marriage and into play dates and home purchases and retirement parties. In these fantasies, my friends and I all moved at the same pace and used phrases like, "Honey, I know exactly what you mean." Though I was dying for them to share in my milestones, I didn't stop to think that they were working on their own timetables.

John and I opened a bottle of wine that night in celebration of my matchmaking retirement. Only after miserable, extended failure did I understand the truth: I couldn't doctor fate. All I could do was sip Merlot and cheer from the sidelines.

For your chance to win a FREE wedding cake and a signed copy of "Running of the Bride" by Rachel Eddey, click here and like us on Facebook.