Dear Wendy
Dear Wendy

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

Last week I watched with eager anticipation the first episode of “The Real World: Homecoming,” a series reuniting the original cast members of “The Real World,” the docu-series that pioneered what we now call reality TV. It was broadcast 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 at the time in Germany, where American TV was, for the most part, limited to whatever shows from the states were aired on the Armed Forces 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” and 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, with the possibilities of life narrowed and 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 had never watched the original series, expressed interest in seeing it – or, OK fine, I may have expressed interest in his 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 had 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.

7 comments… add one
  • MaterialsGirl March 8, 2021, 3:46 pm

    SPILL THE BEANS PEOPLE!!

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  • Ange March 8, 2021, 5:06 pm

    Dated? No. Beaten in a drinking game? Yes.

    I used to work with a girl who was dating a pro footy player here in Aus. At least, she thought she was but he broke up with her by accepting a new contract and moving interstate without a word.

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  • Moneypenny March 8, 2021, 6:05 pm

    I dated a local celebrity a few years back from 2012-2014ish when I was late-20’s. He was a local radio DJ who had been on the air for many years on the local alternative station that I always listened to as a teen/young adult (he is 9 years older than I am). At the time we dated he worked for a different station as the program manager and had a slot on air. Basically on the first date he was telling me about his job without really telling me who he was (like his “radio name”) and I basically blurted, “are you soandso?” and he was like, yeah… And I said I totally knew him from listening from his many years as an on air guy.

    Overall it was pretty fun dating him, we went to a lot of concerts (VIP and all comp’ed) and I met a bunch of people I had known only by name and by voice. Things ended when he was transferred to a station in another city and he wasn’t sure he wanted me to come with him. I’m glad I didn’t go, but I do wish him well.

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  • Rebecca March 9, 2021, 8:15 am

    I had a one night stand in…2002? Yes. With a drummer from Riverdance. He’s lovely, we’re still in touch on facebook.

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  • Helen March 9, 2021, 10:45 am

    When I was young & dumb I fucked around with the first person to be convicted of a hate crime in my state. He was convicted 3 years after I stopped having anything to do with him. Reflecting on my youth is depressing. Where were the adults?

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  • Bittergaymark March 11, 2021, 11:23 pm

    I have lots of famous people stories. Dozens upon dozens of em. But never have I ever dated or slept with any which is quite the sad commentary on my life.

    There was one I maybe coulda slept with. I am not quite certain of this… But my close girlfriend who was dating him at the time remains very much convinced… it’s kinda sorta why they broke up.

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  • allathian March 12, 2021, 6:42 am

    Nope, not even close. But I worked in retail in HS and college and met a lot of fairly famous people in my jobs. Some I wasn’t aware of, though, just a matter of a coworker tapping me on the shoulder asking “didn’t you recognize him/her?” and I’d been completely oblivious.

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