I Met My Husband Through A Craigslist 'Sugarbaby' Ad

Can I spend the rest of my life with someone who slipped me cash on our first date?

By xoJane — Written on Jun 20, 2022

Photo: Getty Images

I had been dating my boyfriend, Peter, for over a year when we were at a restaurant one night and his phone lit up with that email notification while he was in the restroom. I happened to see it (I wasn’t snooping, I swear) and when I got home, I went on Craigslist for the first time to see what on Earth “adult gigs” meant.

It was the thinly veiled extralegal underbelly of an already spotty site — “massages” by the hour, middle-aged (but of course self-described “attractive”) businessmen looking for all-too-personal assistants, and several sugarbaby or sugardaddy ads.

I set up a dummy email address and, being a former linguistics major, responded to three ads that used wording and speech patterns I thought Peter might use.

Within minutes, I had two responses from Peter to my fake email address, asking when I was available to meet for dinner and offering to wire cash to prove he was serious about supporting me.

My head went numb. His ads said he was looking for a girl 25 or younger (I was under 25 at the time), petite (I’m a size zero), in college (I was poised to graduate from Georgetown), and pretty.

But the line that really bit from his ads was, “You should be happy.” Sure, because all the happy girls are sitting at home writing to strangers for paid sex opportunities.

I emailed back and forth with Peter a few times, trying to decipher why he would cheat on me (let alone be so desperate as to pay for it). When I finally confronted Peter, I cried and kept asking him why he would cheat on me in that way. I felt humiliated like I was pegged below the creepiest of strangers he could possibly meet on this sordid website.

He said, "You're too good for me. I don't deserve you," which most readers will probably recognize as a line, but I took as a victory.

I left his condo triumphantly, told the friendly bellman that Peter regularly had hookers over and they should really do something about it, and haven't spoken to him since.

Meanwhile, I’d gotten a voicemail from the third-ad guy, Mark. He had the cutest Southern accent — the voicemail was the nicest thing I’d ever listened to and totally normal except for the offer to “take care of you for as long as you want.” I agreed to meet him for dinner at Charlie Palmer on Capitol Hill.

To be honest, I didn't plan to actually show up. It just felt nice to agree to date since I hadn't been single in over a year and was still very upset over Peter.

We were supposed to meet at seven. At seven-thirty, he called to ask if I was coming. He was so kind and had such a good sense of humor about it that I went to the restaurant out of curiosity more than anything.

Mark ended up being earnest, charming, and strangely wholesome. He was boyishly cute and not anything like I would have pictured a person posting that sort of thing online to look like. I never got around to telling him why I’d responded to his ad — we were too busy comparing stories of our beloved prep schools, which happened to be across the street from each other.

In the weeks and months that followed, Mark would call or text periodically to ask "if there was anything I needed or wanted."

He gave me a set allowance and took me on regular shopping sprees and spa days. I never felt conflicted about this aspect of the relationship. He just enjoyed knowing that I was pampered and well cared for.

We kept dating, and I knew I wanted to stick around for a while when I started using coasters on his furniture. We’ve been married for six years.

The formalized allowance tapered off after we got engaged and added my name to his bank accounts and credit card. He still loves to find any excuse to surprise me with awesome gifts, though.

Sometimes I wonder if our relationship would be stronger if we’d met in a normal or even quasi-normal (OkCupid?) way. But I think there’s something to be said for two people meeting at their lowest point, knowing the worst possible thing about each other, and being able to make each other happy.

Most people show up to a first date thinking of the other person as pristine and only later (possibly even after years of marriage) discover moral or psychological tics.

Mark and I started off our first date with black-and-white evidence of our ethical...flexibility.

Some days I’ll be in the shower or driving and suddenly wonder, Can I really wake up every day for the rest of my life next to someone who slipped an envelope of cash into my purse in the middle of a crowded restaurant on our first date? If we have children, can I tell them to listen to their father because he deserves their respect, and totally mean it?