Singles spend a lot of time fretting over the biggest date nights of the year — Valentine’s Day and New Year’s Eve — but what about the holidays when you can meet those potential dates? Samantha Daniels, a matchmaker and founder of the Dating Lounge, puts Halloween high on that list, calling it one of the two to three best nights of the year to meet someone.
“One of the biggest problems singles have is they hang out with the same people, do the same things and nothing changes,” Daniels says. “Halloween gives the opportunity to do something different, to dress in a costume that puts forth a different side of their personality that doesn’t come out all the time. So why not seize the opportunity?”
Erika Michalski certainly did. In October 2010, she declared to a friend that she was taking a break from dating. She was finishing up a doctorate in education and working full time — and didn’t have the time and energy for anything else. “Everything was pointing against having any sort of meaningful relationship,” Michalski, now 32, told me.
But that didn’t stop her from sneaking her singleness into her Halloween costume. A few days before the holiday, Michalski found a beautiful navy coat with gold buttons down the front and decided she would dress up as Paddington Bear. In the children’s book, Paddington wears a name tag that says: “Please look after this bear” on one side and “Darkest Peru to London, England via Paddington Stn” on the other. Rather than London, the reverse of Michalski’s name tag asked that she be delivered to “the Front Porch of an Attractive Single Man.”
Her Paddington costume wasn’t skin-bearing or sexy — it was just a fun idea she was really excited about, a tactic that Daniels favors. “Don’t choose something that’s cool and interesting but doesn’t make you look good,” Daniels added. On Halloween, she said, people gravitate toward people they’re attracted to, but they’re also drawn to people wearing costumes they’re curious about. “Everybody has a little added confidence” on the holiday, Daniels said. “In some ways, you can hide behind your costume — that gives you added strength.”
When Michalski went to an outdoor Halloween celebration in St. Louis’s Central West End, she ran into that attractive single man she was looking-not-looking for. “You’re sort of perpetually jostled as you walk down the street,” she said, recalling the crowded scene. She was with the friend to whom she had declared her dating hiatus when someone bumped into her from behind. “I hear this male voice say, ‘I’m sorry,'” she told me. “I turned around, and he was the most beautiful man I had ever seen.”
She looked at him and asked a bit rudely where his costume was. (He was on his way to his car to retrieve it.) They chatted a bit, and when he asked for her number, Michalski was sassy and pessimistic: “Of course I’ll give it to you,” she said, “but you won’t use it.”
They intended to meet up later that night, but it didn’t work out. She sent him a text the following afternoon, saying she hoped the rest of his weekend is great. Then … silence.
About five days later, Michalski was heading to Mexico for a wedding; she still hadn’t heard from Dan, her Halloween run-in, and had written him off. When she got back, she landed in Dallas and turned her phone on. She had several text messages from him — first asking her out, then saying she’d been right to ignore him because he’d taken so long to get in touch.
“I immediately called him and left a voice mail explaining what happened,” Michalski said.
They planned a first date, but Dan’s dad was in the ICU with complications from a chemotherapy treatment and he had to cancel an hour before they were supposed to meet. When he called to cancel the date, they ended up talking for more than an hour.
Eventually, they did go on a first date in November and got serious pretty quickly. By the following March, they were walking in that same area of St. Louis where they first met and Dan hip-checked Michalski — a physical reference to the way they first met — “and all of sudden he was on his knee proposing,” she recalled.
Now Halloween is an annual reminder of their relationship — as much, if not more so, as their wedding anniversary. They’ve been dressing in couples costumes ever since they met: They’ve gone as a magician (Dan) with a rabbit in a hat (Michalski); Johnny and Baby from “Dirty Dancing”; and last year they went as Mr. and Mrs. Brown — the fictional couple who retrieved that traveling bear from the Paddington train station — their daughter, Gretchen, dressed as Paddington Bear. Michalski’s mother bought a navy coat before she even got pregnant. “She knew if we ever had a child,” Michalski wrote in an e-mail, “s/he would need to be Paddington at least once.”
And that name tag Michalski wore around her neck five years ago hangs in their bedroom.