Topic of the Day: Have You Ever Dated Anyone Famous (or semi-famous or notorious)?

Topic of the Day: Have You Ever Dated Anyone Famous (or semi-famous or notorious)?

New Here? Welcome! Dear Wendy is a relationship advice blog. You can read about me here, peruse the archives here and read popular posts here. You can also follow along on Facebook and Instagram. If you have a relationship/dating question I can help answer, you can send me your letters at [email protected] (be sure to read these guidelines first). Thanks for visiting!

Last week, I watched with eager anticipation the first episode of The Real World: Homecoming, a series reuniting the original cast members The Real World, the docu-series that pioneered what we now call reality TV. It was broadcast in in 1992, the year I turned 16, and it famously brought together seven strangers picked to live together in a loft (in NYC) to see what happens when people stop being polite and start getting real. I was hooked from the first moment I watched the show 29 years ago.

I lived in Germany at the time, where American TV was, for the most part, limited to whatever shows from the states were aired on the armed forced network, a channel for military personnel and their families stationed overseas (and available to those of us who lived close enough to a base to pick up its signal). However, MTV was part of a European cable package that households that paid for it and/or had a satellite strong enough to pick it up, were lucky enough to view. My household was one of the lucky ones, which meant that I got to watch The Real World at roughly the same time it aired state-side, which was one of the few things that felt like an authentic American teenage rite of passage for someone growing up in Germany at the time. It helped that I loved the idea of The Real World, which in its original incarnation was much more like the documentaries I have come to love and nothing much at all like today’s version of reality TV.

I loved everything about that first season of The Real World – how cool and interesting the seven mostly 20-something strangers picked to live in a loft seemed to my 16-year-old self, the loft itself, and the surrounding New York City. I watched each episode multiple times, had a favorite roommate (Heather) and a least favorite (Becky), and fantasized about living with equally interesting roommates one day, maybe even in NYC. Of course, NYC did eventually happen for me, but not until my 30s, and by then I was neither as interesting as I once imagined I’d become nor as desperate to be. But I still held a soft spot for those original seven cast members of The Real World, a season that, in my mind, so clearly defined not only the 90s, but the Gen X youth experience itself.

At 44, I’m clearly middle-aged, the possibilities of life narrowed, the paths I might still take definitely limited by all the things I didn’t need to consider 30 years ago. And so, nostalgia – particularly the kind that takes me back to my teens and early 20s – is both a welcome retreat from the demands of my current responsibilities (like a weekend visit to my childfree friends in another state might be), and kind of a sad reminder of the paths I didn’t take and the possibilities I’ll now never discover. Nostalgia TV (and film) falls mostly in the latter category for me though, and so I was especially excited to watch The Real World reunion series last week – but only the first episode since, frustratingly, Paramount+ is only airing one a week, I guess?

After we watched the episode, Drew, who never watched the original series, expressed interest in seeing it – or, OK fine, I may have expressed interest in him watching it but he didn’t argue – and so we found it on Paramount+ (I see what they did there), and binged the first 2 or 3 or 8 episodes in quick succession. And then, because it was all I wanted to talk about for a few days, when I met a friend for a walk yesterday, I asked if she ever watched the original Real World back in the day, and, dear reader, she shocked me with the news that no, she never watched it but she did seriously date one of the cast members for three years (they even lived together!)!! I mean, what?! She and I have been friends for almost a decade! How did it never come up in conversation that one of her exes was a cast member of a show that was a defining cultural phenomenon of my – our – youth?

And now I have to ask: who else is keeping famous or semi-famous or notorious exes a secret? Have YOU ever dated such a person? Do you have a Mario Lopez, or a Kato Kaelin, or a Winona Ryder in your dating history? Inquiring minds need to know.