Friendless in Chicago

Tips from a transplanted New Yorker on how to find a BFF in a strange city far from home

Friendless in Chicago

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When Rachel Bertsche moved from New York to Chicago with her husband-to-be, she left behind her two best girlfriends and suddenly found herself without a close friend to call or hang out with.

At her new job at, Bertsche tried to befriend a woman, but her approach, she realized in hindsight, was awkward—either too soon or too aggressive. Bertsche asked the woman if she was free on the weekend, explaining that she had to try on her wedding dress and needed a second opinion. “The look on her face reminded me of the male lead in a romantic comedy when the girl says ‘I love you’ too soon. It was a startling combination of fear and confusion and whoa-slow-down-there-lady.” Berstche gave the woman an exit strategy and she took it.

Bertsche considers these perils of befriending in her debut book, MWF Seeking BFF: My Yearlong Search For a New Best Friend.

In the book–which is part memoir, part advice–she reminisces about the ease of making girlfriends when you’re young and thrown together in what she describes as the “relationship breeding grounds” of high school and summer camp. By the time a woman is in her late twenties, she argues, making friends is not a natural process. “In fact, I’d completely forgotten how to do it.” She knew what she was looking for, a friend she could call and say, “ ‘What are you doing today?’ But getting to this level is tricky. At what point after meeting a new friend is it acceptable to call ‘just to say hi?’ When is it not overly aggressive to text, ‘Pedicure in a half hour?’ ”

Bertsche’s befriending missteps taught her that it’s best at first to use text-messaging when getting to know a colleague outside of work. Don’t phone her. Phone calls require lots of small talk and can be screened if co-workers think you’re calling about work.

Invite a colleague to an after-work drink. “Keeping it on a weekday seems less invasive of her personal time, but gives you a chance to establish your off-hours relationship.”

Outside of work, Bertsche began to email women she’d met only briefly, such as the woman who did her wedding makeup and the woman she made paella with nine months earlier in a cooking class. “In all of these cases, we vowed to get drinks one day and never did.” Bertsche revised her tactic. Instead of taking “the needy girlfriend approach,” she went for “confident fun woman open to new things.” She emailed each female acquaintance with the phrase, “We talked about getting together, which I’m finally making good on.” That wasn’t desperate, Bertsche insists, but rather “follow through.”

For every decline she got, she made a counter-offer. If the person wasn’t free on Saturday, Bertsche wrote back suggesting a different day. If that first meet went well, Bertsche asked for a second one. “There’s a theory in social psychology called the familiarity principle. The more you see someone, the more you’ll like her.”

She reminds her readers, “Women are used to being the askees, not the askers. We want to be pursued.” For the dates with potential, Bertsche followed up at least once; two or three times if she really wanted the best-friendship to happen. After three emails, “If she still isn’t reaching out I can give up. It can’t be a one-way street forever.”

Bertsche even tried a variation of speed-dating called speed-friending, and was impressed that there were no outcasts or misfits. She met four women she wanted to see again. At the end of the event, the host announced, “This is friendship. There is no playing hard to get. There is no two-day rule before calling back.” Each participant had to promise, out loud, to immediately make date arrangements with any woman they hit it off with.

Has she since found a best friend forever? Bertsche did find a lot of new friends. “A number of those friends have become very, very good friends,” she says in an email. “One day, when we have years of friendship under our belt, they might be BFFs!”

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