Last summer, I finally tried my hand at dating apps. I had regrets.
Like this guy I met up with at Betty Rae’s Ice Cream Shop. All he talked about were his AP classes in high school. For the record, he’s not in high school.
Another asked me out to IHOP (classy, right?), but he was a college drop-out who wanted to become TikTok famous and, in his free time, posted skateboarding videos for his 11 YouTube subscribers. I wasn’t convinced our futures were aligned.
Guy number three was a sweetie—mama’s boy, videography major, had a cool internship lined up to do promo for Chicago Fire FC, Chicago’s pro soccer team, but I felt like I was missing that chase factor.
So, I quit. I gave online dating a run for its money, but clearly, my three summer love interests were a bust. So, I was done. All dating apps: deleted. What did I do wrong?
It’s been a year since quitting. So, to celebrate that special anniversary, I decided to perform a little social experiment. If I couldn’t find the man of my dreams, what if my moms could? It’s like modern arranged marriage but with a little je ne sais quoi—and by quoi I mean my 58-year-old moms would be posing as their 21-year-old daughter and flirting with 20-something men on a dating app.
LET THE FISHING BEGIN
I just want to say this: I trust my moms. They know me more than anyone on this earth. My likes, dislikes, passions, even my sense of humor, and the kinds of things I post on social media. They’ve seen the guys I’m into, from adolescent crushes to more recent prospects. If they couldn’t find my Mr. Right, I at least trusted that they could find me a nice guy with good morals. A family-loving, ambitious hunk. Like the big-body, hairy, manly-looking types they always point out to me, even if I’ve always preferred the leaner, babyface type.
In the beginning, my moms were not happy. I told them the rules were simple: talk to guys for two weeks, pick a winner for me to Facetime at the end (Covid’s still a thing, after all). But they hated the idea. It took some teeth pulling before they finally complied. Both helped build my profile, but only one, Sherri, did all the texting, “Kaili, do you know how embarrassing this is, not to mention how many lines it’s probably crossing? What if someone finds out it’s me, an old woman, texting them and I get reported?” I reassured her that all would remain harmless.
My other mom, Stephanie, got a hoot out of it. “Sherri, just say ‘ha ha ha’ and send smiley faces like [Kaili] does. Maybe throw in a little winky face.”
I walked them through setting up a new profile on Hinge—I’ve found it has the simplest user interface. Bonus: They won’t even have to feel pressured to make the first move.
They had full discretion on which photos to use, my interests, my taste in men. I will say, they nailed it with the photos: cute and casual, nothing too modest. Although, they did make the bold decision to include only individual photos. For me, profiles like those were always headscratchers. Like, does this person have friends?
For the Q&A, a prompt asked what I like to do in my free time. Perfect opportunity to talk about doing fun photoshoots with friends, picnics, and taking walks, right? What I got was, “I like relaxing and hanging out with friends.” Can a response get blander than that? And the period killed me.
Once my profile was complete, we ran through a few quick scenarios before I left the fate of my love life in their hands. Of course, the next morning I received tons of texts from Sherri, who was flipping out. “Kaili, I can’t do this. This is so embarrassing. You got 14 likes. One guy said ‘nice puppp.’ WHAT am I supposed to do with that? Another one sent you a rose. What does that even mean??? I don’t like all these men looking at MY daughter.”
I calmed her down and said she only needed to respond to who she felt comfortable with. Knowing her, it was probably going to be a goodbye to “pup guy.”
The impromptu FaceTime calls about “all these weird men” who were trying to take me on a date continued. One day it was a guy who had memes overlaying all of his photos. Another day it was someone who had, “Hey my name’s Microsoft. Can I crash at your place?” in his bio. Sherri said, “I read that and was like, ‘Um, no! You will not be sleeping with my daughter!’” I started to feel bad for my moms. They had to see what slim pickings there are for men nowadays. Embarrassing.
Although she had some bad days, every now and then she’d throw out comments like, “I’m really hitting it off with Tyler.” Then Stephanie would say, “Be careful Kaili, Mom might find herself a new boyfriend.” Then they’d laugh. I think they were starting to have some fun.
Once the two-week period ended, Sherri was more than ready to be done. I asked who her favorite conversation was with. The lucky winner was named Isaac, “Kaili, get this. He’s a fiction author, 23 years old, doesn’t drink, doesn’t smoke, no weed, and he’s really cute.” I logged into Hinge to get a look at the guy.
Eh. I called it. I knew she’d choose the hairy hunk type. But after logging in and reading through some of her other matches, I was fairly pleased with the overall pick.
ENTER ISSAC
I opened the conversation between Issac and my mom (now me) and scheduled a Saturday night FaceTime call. Minutes before our start time, I checked the battery on my phone: 21 percent. Perfect. About 30 minutes of easy get-to-know-you questions, a little banter, lots of smiling and nodding. Then, I’ll use my phone dying as an excuse to get out of the call. I didn’t have high hopes.
Issac told me all about his career working at a Chicago-based publishing company, how he prefers writing over publishing and his return home to Iowa. He’s a family man, had a good sense of humor, and had a good head on his shoulders. Well done, moms. We bonded over writing and the thrill of running with a good story. Little did he know he was my next main character.
The 10 percent battery remaining notification popped up, and I knew I had to wrap things up. But of course, the elephant in the room—or at least of my inner monologue—was do I tell him? How do I tell this kind man that he’d been talking to my 58-year-old mother this whole time and that she “chose” him to be my final rose? And to make the matter worse, I’d already made the executive decision that I was not interested in pursuing a relationship with him.
I told him the truth, not because it was the right thing to do ethically but because he’s a writer. I figured he’d understand doing what it takes for a good story. His bubbly spirit also made me assume that he wouldn’t be mad.
I told him I had to tell him something and asked that he not be upset. I introduced my crazy idea of letting my moms run my dating apps and how I wanted to test it out. I strategically spoke in run-on sentences, fearful of giving him air space to chime in. I watched his face as the puzzle pieces slowly fell into place. He chucked, “Wait, so they chose me? Am I the lucky winner?!”
He wasn’t upset at all, “I totally get why you did it, like as a writer, and I didn’t suspect a thing the whole time. I’ve never heard of anyone doing this before, but it sounds like you guys had a good time, and that you got everything you need for the story. And I guess thank you to your moms for choosing me.”
Then came the question I knew was unavoidable, “What is it that you’re looking for exactly? Did they pick a good one?” I let him down easy by saying I wasn’t seriously looking, which he respected. The silver lining, we agreed, was that now we both had a cool-ass story to tell.
Did my moms find my Mr. Right? No, but Issac and I said it best ourselves. We have a story that probably not many other people share. This experience was quite the ride. A lot could’ve gone wrong, but thankfully my moms were troopers and pulled through. It was the perfect, craziest, most ethically challenging, and entertaining party to my anniversary of being painfully single.
