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Authors: Rachel Bertsche

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I don’t think it’s a coincidence that my dates have gotten more successful now that I’m choosing them instead of letting them choose me. And yet, when I catch wind of a local friend matchmaker, I’m pretty eager to hand over the reins.

Joe Drake prefers to be called a friend broker. He compares himself to a real estate agent, but instead of finding you
a house, he’ll set you up with a friend. I found out about his service, Meet Joe, through a recent article in
Time Out Chicago.
Like Saya Hillman, Drake is a connector. The 31-year-old entrepreneur has contacts all over town, and now, for only $29.95, he’ll introduce me to a few of them.

I signed up for the service as soon as I read the
TOC
profile. If I were more narcissistic I’d think the local Chicago area was learning about my search and creating companies just for me. And while, yes, hiring a matchmaker goes against the concept of culling through the friend-options and picking the perfect fit myself, it might be even better. I’ll meet with Drake, he’ll get a sense of my winning personality, and find me my Princess Charming. No glass slipper necessary.

We meet at the local Argo Tea. In his email, Drake said I’d find him because he is “an Asian guy, which usually separates me from the crowd, and I’ll have a little computer with me.” I immediately spot him and would have without the description. He has an air of friendliness. While others are hunched over their computers, shut off to the world, Drake is sitting up, almost smiling at his laptop. Malcolm Gladwell writes in
The Tipping Point
that the defining characteristics of connectors is not only that they are embedded into many different subcultures, thus making acquaintances far and wide, but that “their ability to span many different worlds is a function of something intrinsic to their personality, some combination of curiosity, self-confidence, sociability, and energy.” This is why, despite embedding myself in various social circles this year, I may never become a full-fledged connector. While I am becoming friendlier, it’s still a conscious choice. I think to myself “I should talk to this girl in yoga instead of pretending I don’t recognize her, that would be the nice friendly thing to do.” It’s not my natural instinct. With true connectors, it’s a reflex.
Forging new connections is as innate to their personality as singing butchered show tunes is to mine. We can’t help it.

The energy that Gladwell describes radiates from Drake. As soon as we start talking it’s clear why he’s so socially integrated. He’s magnetic—not in an “I want to sleep with you” kind of way, but more of an “I want to hang out with you and soak up some of your positive vibe” sense. He’s charmingly dorky, and strangely easy to talk to. Drake, like Hillman, seems to relish making new connections.

Five minutes into meeting I realize I’m telling him my entire life story, not that he asked.

“Sorry, you’re supposed to be interviewing me, not listening to me ramble on,” I say.

“No, this is good. I’m just trying to get a feel for who you are.”

I feel like I’m in therapy.

“Tell me,” he says, “what kind of friends are you looking for?”

“Um, nice ones?”

“Well, tell me about the local friends you have, or what’s missing from your local network.”

I give Drake the full history—that when I started this search I had some local friends who went to Northwestern with me. That while they were all best friends with one another, I was the “other” one. That we made dinner plans once a month, but I didn’t have a local friend I could call just to say hi.

“Why didn’t they make it over the hump do you think? What makes your best friends your best friends?”

This is the toughest interview I’ve ever had. I was prepared to tell him my favorite books and TV shows, but there’s more self-reflection required than I anticipated.

“My best friends, well, they’re all … fun. They love pop culture. They’re easy to talk to. But we can sit around watching
TV without talking, and that’s fine, too. We laugh a lot. I always say I want friends like the girls in
The Babysitter’s Club
, that kind of bond.”

Drake nods, but I start to second-guess myself.

“I feel like I’m making myself out to be a real teenybopper. I swear there’s more to me than my love for
Entertainment Weekly.

Thank God this isn’t a job interview.

“Well, if your friends—ones who didn’t know one another—were to explain you to me, what would be the thing they’d all say?”

It’s a good question, and probably one I should have asked myself before I started this search. “You know what it is? I think they’d all say that I don’t take myself too seriously.”

For the second portion of our interview, Drake gives me a bunch of different scenarios. “Imagine your new friend calls and suggests these different activities for a Saturday,” he says. “Then tell me how you would react.”

“Okay.”

“Go to the movies …”

“Sounds great.”

“Take a trip to the casino.”

“I’d say ‘when can you be here?’ ” Drake is surprised. “I come from a long line of gamblers,” I say. He’s taking furious notes.

“Go to a standing-room-only concert of an up-and-coming indie band you’ve never heard of.”

“I’d say okay because I try to make it a policy to say yes to everything, but it wouldn’t be my first choice.”

“Go to the newest, hottest club and get bottle service.”

“Well that’s just silly.”

* * *

Drake and I say goodbye after ninety minutes of soul-searching. I’m almost sad to leave. Our meeting brought some unexpected clarity to what I’m looking for from this year and from friends in general. It was the first time I’ve really probed my own role in friendships, rather than focusing on what other people bring to the table. It’s something I should have thought about months ago.

My thirty dollars bought me this meeting plus one setup, but Drake usually tries to wrangle a group of three or four for the first date. If after that I want to meet even more people, I’ll have to fork over additional cash.

Given how thorough he was with his questions, I have a feeling he’ll nail it on the first try.

I leave our meeting with a promise that I’ll be matched within weeks, and lyrics from
Fiddler on the Roof
running through my head.

Last weekend, the day before girl-date 35, was my first wedding anniversary. I had originally planned a friend-free day. In the ongoing effort to balance marriage and friendship, the first anniversary was a no-brainer.

Until Matt forwarded me an email. The purpose of the forward was to clue me in on our friend Sergio, who lives in Mexico City and only checks in occasionally. I, being the normal curious wife that I am, figured it would only make sense to scroll from the bottom up and read the entire exchange between my husband and his friends. That’s not violating privacy,
right? He’s never been a master when it comes to technology, but if there were any secrets he’d surely delete them.

It made for some interesting reading. The most fascinating part was the discussion of when they should hold their annual fantasy football draft. In a note from Matt to his pals are the words “My vote is anytime on the 29th.” August 29th, of course, is our anniversary.

I drafted an email of my own. “You pushed for your draft
on
our anniversary? Do you not understand how anniversaries work? I know this is your first one, but let me explain: You spend them with your wife.”

I wasn’t mad so much as amused. It was pretty obvious that Matt had forgotten the date entirely. By the time I caught wind of his slipup, there was no fixing it. So when our special day rolled around, he camped out at his computer and I invited over some entertainment of my own. Jillian, Paul, and the twins.

The gang showed up just after 11. Luckily my mother still has the matchbox cars from my 31-year-old brother’s childhood days, so the twins had something to play with. That is, when they weren’t running around the track that is my apartment.

I never realized that my home’s layout lends itself to running in circles—through the kitchen, through the hallway that wraps around the kitchen, and back through the kitchen again—because who runs circles around an apartment? Two-year-olds, that’s who.

We feasted on bagels and cupcakes—I like to keep things nice and low-carb. It was a fun morning, but the highlight came at the end.

“What are you doing next weekend?” Jillian asked. Labor Day was coming up and I had nothing on the schedule.

“Not much. Living it up on a three-day weekend.”

“My parents are coming and they’ve been dying to meet you. Want to come for brunch Monday?”

“That’d be great!” My first offer to meet the parents—from Kim a few months back—fizzled when she disappeared. This gave me a second shot at the friendship milestone.

A week later, I’m in Jillian’s dining room, checking out her father’s family photo calendar and giving her mom book recommendations. Jillian’s mother, with her curly blond hair and tie-dyed T-shirt, would be the perfect best friend for my own, if only she didn’t live in Connecticut.

We sit around the table eating cinnamon buns and granola, watching the boys play the drums with their sippy cups. It feels not unlike the Sunday mornings of my youth, those post-sleepover breakfasts with my BFF-of-the-moment’s family. Besides the fact that this time around my friend has a husband. And diaper duty.

CHAPTER
11

This evening I’m going speed-friending. Yup, speed-friending. It’s like speed-dating—where you meet a variety of potential partners for only two minutes each—except this here’s an all-female affair. The event is hosted by GirlFriendCircles, the same organization with the ConnectingCircles and the Table Tent and Logan, the energetic whirlwind I went out with earlier this summer.

I hate to admit this, but I’m dreading the whole thing. I’ve worked hard to become more open-minded and not write off potential friends before we meet, and overall I’ve been fairly successful. But there are moments when I can’t stop myself. Like tonight.

Before this year I never would have signed up to speed-friend. It would have seemed too desperate, too contrived, and too unlikely that I’d connect with anyone who could really be a BFF. But once I decided to dedicate this year of my life to forging friendships, I committed to doing everything I can—no matter how scary or pathetic or absurd it seems. You never know, right? And I can’t conduct a complete search without
following every lead. (Don’t say all those
Law & Order
marathons never taught me anything.)

In keeping with my resolution, I eagerly signed up for speed-friending as soon as registration opened up. Now that it’s tonight, there’s a question repeating itself over and over in my head:
What kind of person signs up for speed-friending?
Well, me, for one. But why would someone who
isn’t
deliberately test-driving every meet-and-greet method want to do it? I’d be lying if I said I’m not anticipating finding a bunch of weirdos.

I am the first to arrive. I’m about fifteen minutes early because I was worried about finding a parking spot, but also because I was excited to meet Shasta Nelson, the GirlFriendCircles founder, in the flesh.

Nelson is every bit the friendship enthusiast in person that she was on the phone. She has a dirty blond bob and is noticeably fit, wearing jeans and a neon pink GirlFriendCircles T-shirt. She immediately envelops me in a hug—we’re like old friends by now—and I congratulate her on the company’s spot on
The Early Show
this morning.

“It’s a start,” she says. “There’s definitely a market of women out there just like you.”

By the time we get going there are twenty women in attendance, two of whom were in my original ConnectingCircle. We’re separated into groups, under 40 on one side of the room and over 40 at the other, and seated at tables of three people each.

“Each of you has been given a form to help keep track of who you meet,” Nelson explains. “After each round, fill in something about the person—red sweater, loves to travel—that will jog your memory. Then, when you find out who you matched with in a few days, you’ll remember who she is.”

Nelson says she’ll give us a different question every round, and we each need to answer for two minutes. During those two minutes no one else is allowed to talk.

“For some of us it can be hard to talk about ourselves for two full minutes, but you are all interesting people! You have lots to say!”

The questions are softballs: What do you love about where you live? What do you like most about your best friend? What’s an activity you’re interested in learning or wish you did more of? Who in your family do you most resemble? Personal enough to give others a sense of who you are, but not so hard-hitting that it feels like an inquisition.

As is almost always the case, the women I expected to be a group of misfits turn out to be perfectly interesting, nice, friendable people. I should have known better.

In fact, I’d like to meet at least four of the women again. Erin does lighting for a local dance company and loves to travel. Nicole works in finance and is an amateur photographer. Susan is dying to take trapeze lessons and is an aspiring cook. Keisha says she’s here because her best friend in D.C. is her go-to phone call, and she’d love to have that relationship locally. No kidding.

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