Everyone Has a Roster Now and I Kind of Hate It

When I was recently visiting my best friend and her family in Dallas, Texas, her mom, Debbie, told me I needed to be dating “a Rolodex of men.” She wasn’t one of those moms just talking out the side of her neck with unwarranted advice—Debbie knew ball. Before meeting her now-husband of more than 30 years, she herself had been juggling four men when she bumped into Mitch while waiting in line at Lover’s Eggrolls. Immediately she knew she had met the one. The next week she went ahead and broke things off with all four of her other bachelors and gained a boyfriend she’d go on to build a dream life with.

As she told me all of this, my initial reaction was, Okay, Debbie, you queen, I wasn’t familiar with your game. But maybe her success—happily married for decades with two gorgeous daughters—was due to her approach to dating.

A hopeless romantic and true lover girl at heart, I’ve always been the type to fall in love too quickly, becoming enamored with a fantasy I’d built in my head versus the actual person. Having a roster, as my peers call it—because what even is a Rolodex?—could be the perfect solution to this, I thought as I listened to Debbie detail her delicious dating escapades. Essentially building a fantasy football league of romantic suitors and dating each of them in a synchronized rhythm until, ideally, I connect with one over the rest and we settle into a monogamous relationship together? I could get behind that kind of happily ever after. After the visit and gleaning all of Debbie’s wisdom, I immediately resumed swiping on the apps, hoping to build a lineup of men better than this 2026 Knicks Finals team.

I approached my roster like a full-time job. And boy, was I working. 

The concept of having a roster has intrigued me most of my adult life. But as I began curating the men who danced across my dating apps, a feeling of doubt crept in. How big could my roster grow? How many guys do I need to be dating for it to even be considered a roster? After rewatching a season 3 episode of Friends, the one where Phoebe juggled dating two guys, I decided that my roster could consist of as few or as many men as I could manage. With an I’ll-try-anything-once attitude and a mentality of there’s less room to get hurt when you’re not fully committed, I approached my roster like a full-time job. And boy, was I working.

I overanalyzed profiles like a hiring manager looking at resumes. I swiped so much my thumbs felt numb. And my nights were consumed with virtual chit chat. I was utterly exhausted simply trying to create my roster—my social battery is only equipped for so much ‘getting to know yous,’ gauging who’s down for what, and who’s into who—not to mention who even is who. The doubt turned into anxiety next. Who was I kidding? I can barely handle texting all of my friends back in time, let alone keeping track of multiple conversations, personal details, and faces to match with all of it. With Debbie’s directive and fairy tale outcomes ringing in my ears, though, I continued on my mission.

Intentionally starting a roster while also trying to intentionally date was presenting itself as an insane paradox.

I went on a handful of dates. I grabbed drinks with Dave*, then a couple days later I got breakfast with Kai*, and shortly after that, I went to the movies with Jake*. Dave was the only one who secured a second date. In all of these experiences, I had the same conversations again and again, and I was kind of annoyed and bored. Quickly, I realized just how inorganic this felt to me. Intentionally starting a roster while also trying to intentionally date was presenting itself as an insane paradox. How could I keep seeing Dave, try to grow an honest connection with him, and then introduce new men into my life? As a girl who’s only ever been single or in a monogamous relationship, playing the field like this felt misaligned. It felt like forcing myself to try a viral makeup technique that didn’t really work for me and then wear it out of the house. Even more off-putting than that, dating like this made me feel no better than the shitty men of my past, the ones who hurt me and kept me on the sidelines while they kept their options open. I didn’t want to be among them.

I had been collateral damage in what I was attempting to play out. My desire for a roster might have been an attempt to reject a sideline role and be the one with “Main Character Syndrome” for once. In the game I had started to play in my head, every person I dated could simply be a recurring guest star in the show that was my life. If I was the main character and everyone around me could be “recast” at a moment’s notice, my ego never had to bend and I could be incredibly self-centered without consequence. In rostering, I never had to be vulnerable, and in turn, I never built true intimacy. And, by discarding people as sideline characters, I never had to truly face myself. I could rotate to the next guy as soon as one started reflecting my own flawedness back to me.

I accepted that my version of casual dating did not need to involve more than one guy at a time.

If true love requires genuine acceptance and sacrifice of the ego, then roster dating the way I was doing it is the definition of avoidant attachment (the insecure attachment style characterized by a deep discomfort with emotional intimacy). For what it’s worth, there’s probably a very intentional, loving way to have a roster in which all parties have agency, but I was definitely doing some projecting of my past experiences in my version and it wasn’t healthy. I accepted that my version of casual dating did not need to involve more than one guy at a time. The timing of this revelation worked out, too, because my roster died before I could kill it when Dave ghosted me before our third date. Womp, womp.

While rostering isn’t for me, I see both why and how it works for others. Debbie’s daughter, my friend Alice*, also gave it a try around the same time I did. She saw it as a form of speed dating before settling down with one guy. At one point, her roster grew to roughly three men she successfully split her time between, and she has since met a man she wants to date exclusively. Many of my friends love dating this way. They thrive in this sense of autonomy, and view these short-lived, overlapping flings as great forms of education, teaching them more about themselves, what they want, and what they don’t want.

How could this be the norm for my generation, my friends, and those before me, but not me? I started to feel like I had done something wrong. Reflecting on my roster, maybe forcing it was the issue. A roster of my own doesn’t seem forever impossible. However, my lingering desire to manage a Debbie-level Rolodex feels like a sophisticated coping mechanism for a lonely digital age, like putting a bandaid on my insecurities and carrying on with my life. I know that beyond that, I have the desire and the will to bare my flaws and love wholly and deeply, with one person at a time or potentially a roster (if texting back in a timely manner gets easier for me).

*Names have been changed.