I never thought I would end up with a zaddy. For the uninitiated, Urban Dictionary defines a zaddy as “an attractive older man who is fashionable or charismatic.” Otherwise known as the gorgeous guys in Rolex commercials who look like they know exactly where your clitoris is. Celebrity zaddies include Brad Pitt, George Clooney, Idris Alba, David Harbour, Barack Obama, Pierce Brosnan, and, in some cases, Steve Carell (to each their own!).
Prior to my foray into zaddydom, I had always dated guys in their 20s or early 30s. They usually had three other roommates crammed into a tiny New York City apartment, wanted to black out every weekend, and didn’t have the faintest idea what they actually wanted to do with their lives. Oh, and they still wore clothes that their mom bought for them from TJ Maxx. For the most part, these
men boys were funny, good-looking, and served as nice fodder for my Instagram feed, but I never felt like they were husband material. They were projects that had potential, but I was bored of fixer-uppers.
For cis females, finding a man to date is kind of like adopting a pet. There are the cute, young puppies who are adorable but untrained—the ones who accidentally bite your fingers and sometimes get so excited when you pet them that they piss themselves. Then there are the older dogs, who notably aren’t running around humping everything that moves. They are tired and have arthritis. They are also pre-trained from their previous owners, so they won’t even think about jumping on your couch. Even with their flaws, you know what their personality is. But with the young puppies, you don’t know what they will become. They could get into crypto! I digress.
I was 28 years old when the pandemic hit and, like so many of my peers, I moved in with my parents—and five cats—in Shelter Island. My dating life was bleak. I was FaceTiming with a former pro football player I met on Raya who was partying in Miami every night, then calling me to say how he wants to see me, but neither of us would commit to a plan. I was also in a toxic situationship with a guy I met from a reality TV show who called me to talk about his feelings multiple times a day, got jealous if he heard I was talking to other people, and would occasionally beg me to go on Instagram Live with him so he could flirt with me publicly and get more fans. Another guy told me that he didn’t believe in therapy and just “needed to spend more time in the woods with wolves.” Suffice it to say, things weren’t going well.
My mom was seriously starting to worry about me and my ability to meet someone normal. I told her that no one had “gotten away”—I just hadn’t met my person yet. (I hate that I just said “my person” because it sounds like a bad Instagram caption, but I really believed that when I met my future husband, I would know pretty quickly. My parents got engaged after only five months of dating, so I had that love story in my head for myself, too.)
Then, one particularly boring day, I got a message from [The Real Housewives of New York City star] Luann de Lesseps asking if I wanted to get an outdoor, Covid-safe lunch with her. I was starstruck that a reality TV icon wanted to chat with me, so I changed out of my oversized spaghetti-stained depression T-shirt and headed straight to her. I posted a photo of us on Instagram (because if you don’t post it, did it even really happen?) and tagged the location as Shelter Island. That night, I got a message from my future zaddy.
To be clear, this wasn’t a random dude in my DMs. I had actually seen him perform at the Comedy Cellar six years earlier and thought he was very handsome: tall, with great cheekbones, thick silver hair, and a sexy low voice. Unfortunately, he lived in Ireland at the time, so I figured it would never work out between us (and therefore didn’t try to talk to him after the show). A couple of years later, when I got into the comedy scene myself, he started following me on Instagram. I followed him back, but we never spoke, mainly due to the distance. Turns out, when the pandemic hit, he had moved back to New York.
The DMs went like this:
Zaddy: Are you out East?
Zaddy: Do you want to get coffee on Friday?
Me: Yes, here are my digits.
That was it; no games. It was refreshing! He was 45, which is 10 years older than any guy I had ever been romantic with up until that point. He picked me up for our date in a black BMW convertible, and I remember immediately feeling calm with him. When we sat down, it was clear that he was interested. He asked me all about my tennis career and how long I’d been doing comedy. I found out that he lived in China for two years and first learned how to do standup in Mandarin. He’d been to therapy. He loved his career. He’d also been sober since age 19, and I found that super attractive. No drunken fights? Staying in on the weekend and eating good food while watching cult documentaries instead? Sign me up! I discovered we were both from New York City, loved #sports, and had the same silly and dark sense of humor. He didn’t go in for a kiss at the end, and I liked that. I was emotionally connecting with him while wondering deep down what it would be like to date my first silver fox. After talking for a while, he asked me to play golf with him later that week.
Thankfully, I have some old man tendencies of my own (namely, I enjoy golf, tennis, and napping at inappropriate times), so I was excited for our second meetup. When we arrived at his golf club in Westhampton Beach, everyone knew him. Watching him shake hands and exchange inside jokes with people there was mature and undeniably hot. He had this whole life without me, and it seemed like he was doing pretty well. I didn’t see anything I had to fix so far. During our round, I wound up scoring an eagle (that’s golf lingo for two under par) on the sixth hole, and he was so proud of me. In fact, he bragged to all of his friends afterward. It was cool to see a guy who wasn’t intimidated by or competitive with me; instead, he was showing me off. So, naturally I asked him if we could go back to his house.
Disclaimer: Given the stay-at-home orders, I hadn’t been touched by a man in 7 months, and had spent no less than 45 minutes shaving my entire body—from my belly button to the top of my toes—in preparation for this event. I was ready, to say the least. He brought me to the beach, where we laid down on two towels and had our first kiss. (I feel like this is turning into an erotic novel, but I’m into it.) Then, he brought me back inside, and we did the deed. It was different, but in a good way.
Sex in your 20s can be chaotic because young guys are still figuring out what they’re doing (there’s a lot of jackhammering and a lot of, “Did you cum???”). This man knew exactly what he was doing, and he cared about what I wanted as well. I tried to give him the “I don’t normally do this on the second date”-type speech right after, and he immediately rolled his eyes and shut me down. He liked me, and that was that. Did I mention that he played the New York Times crossword puzzle on his phone right after? I had finally found what I didn’t know I’d been looking for.
We spoke every single day since he first DMed me, and we were engaged within six months. My parents immediately loved him because he was driven, smart, kind, financially stable, loved me for me, and they could talk about the ’80s together. My friends loved him too—they called him “Caddy Daddy” and said I had never seemed happier. They were right. I really respected his brain; he gave me great life advice, and I felt like I could really be vulnerable with him. We were emotionally intimate in a way that I had never been intimate with a guy before.
Things got complicated when he visited me for three days while I was shooting Summer House. Some other cast members weren’t kind about the relationship; they called him old and made fun of his gray hair behind his back. When I finally posted a photo of us on social media, there was a ton of positivity, but also the occasional “is that your dad?” comment. Overall, I didn’t care what people thought, because it was all low-hanging fruit. I was 29 and he was 45, and it just felt right.
Warning: There are some red flags to consider if you are looking for a zaddy of your own. Mainly, it’s of crucial importance that there isn’t an imbalance of power. If they make a lot more money than you, or if they act like they always know better than you, that can be problematic. You never want your partner to feel like they have control over you. You want to feel like equal partners navigating life together. You also want to make sure that you have a lot in common besides physical attraction. If you want to talk about The Kardashians and he just wants to talk about NPR, that could get old really quickly.
If you think you might be interested in meeting a someone older, the first step is raising your age range on your dating apps. If you’re in your mid-twenties, raise it to the mid-forties and see how it goes. Continue to be yourself and do things that you enjoy, but once you become aware of older men, you will start to see them everywhere. They are at dog parks, coffee shops, and very often in the Advil section at Walgreens. Happy zaddy hunting!