Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

That’s Entertainment

Thats Entertainment just a story  NYC Times Square wide angle 300x224I’m 40, dammit. 40. I have no idea how many dates I’ve been on in my life, with how many different men, but suffice it to say we’re talking deep into the triple digits.

And that’s something I’m neither proud nor ashamed of. It just is what it is.

But 20+ years of dating, all of those men, and there are still some questions I don’t have the answer to.

For example, does and/or should a guy’s job matter. Yesterday, I came across this post in , “Judging a Guy’s Dating Potential by his Job.”  Which on the surface, sounds kinda harsh. But then it talks about Health.com’s list of “10 Careers with High Rates of Depression”.  And that’s pretty legit.  Some careers do have much higher rates of depression. And it’s not unwise to take that into consideration, I guess.

But, beyond basic stats about depression rates? I’ve already established that my preconceived notions about guys who work in finance were unfair.  Am I ready to let go of my other “issues”. Or rather, my one big issue.

I’m fairly sure I’ve written about this before. At least once or twice.  I have a history. A not great track record. With guys in the entertainment industry. I don’t go after guys in those fields.  Far from it. I live in NYC. They’re pretty much everywhere.  I’ve always had friends who worked in theater/tv/film/music… and for whatever reason I’ve dated quite a few of them.  And no I don’t really want to go into much detail here.

Anyway, I’m starting to think (AGAIN) that I should stop dating them. It’s not just the musicians and actors (although that’s a no-brainer that I fall down on at least 1 or 2 times a year).  It’s the behind the scenes guys. The producers, writers, makers and doers of all kinds.  The successful ones are all (warning – wild generalization) wonderfully charismatic.

They woo so well.

Anyway, I mention this now because I’m likely going out with one of them this week. Unless, of course, I decide that no good can ever come of me dating a guy in the entertainment industry.  That I should learn from past mistakes and not even bother.


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8 to “That’s Entertainment”


  1. Terry says:

    I married a TV executive producer – but what works for one won’t necessarily work for another. Most of my dating career was with women in the health care field- from doctors to nurses, to – well – you know.
    Perhaps trying a different field isn’t a bad thing- but then again I think it is random. It was random that I met my wife – it was random that we happened to get along- and the only thing planned was our son.
    Stories- we have lots of stories – good and bad and the lessons we learn are – -well – I don’t know.
    I do like being with someone of a different perspective, though – because with my wife I have something I had been missing – a team.

    • Simone Grant says:

      Funny that you mention that. The guys who I’ve always been least attracted to are guys who’s work and way of thinking are most similar to mine. I love that difference of perspective.

  2. Matt says:

    I wish more girls would want to go out with “regular” New York guys. I’m a regular NYC guy, who is often dogged out by girls who are looking for someone in the Entertainment or Arts.

    It definitely works both ways there.

    • Simone Grant says:

      I’m sure it does. It’s a big city, lots of people, and each of us have our own perspective and prejudices. I meet a “regular” guy who keeps normal hours and doesn’t expect the whole world to revolve around him and I’m in heaven. Another woman might pass him by. It takes all kinds.

  3. I think that getting caught up in whether to date “this guy” is really counterproductive. Because nobody is really just their job. If what you’re saying is that you don’t want date people with weird work hours or egocentric people or creatively driven people, that’s one thing. That’s specific. I don’t know if “entertainment field people” is specific enough.

    • Simone Grant says:

      You are, exactly, right. It’s not the job but the character traits and behaviors that usually come along with it. I love being around creative people, and can even live with the odd hours (as long as I’m not expected to reschedule my life around them, which is what I usually end up doing). But I have zero patience for the narcissism, materialism and arrogance that I’ve put up with in the past. But it’s not fair to assume all people in the entertainment industry are like that, as I have many friends who aren’t….

  4. Elizabeth Andrews says:

    I live in LA, and I’m 40, and I have this same problem. My entire life I’ve been drawn to “creatives,” particularly writers, filmmakers, and comics. It’s one of the reasons I moved to LA, but I think it is also a contributing factor to me still being single.

    My take on it is this: men in entertainment are either still struggling, and thus unable/unwilling to commit/settle down, or they’ve “made it,” in which case they want to take advantage of their fame and fortune by dating lots of nubile, hot women and/or marrying eye candy. It seems you can’t win.

    That said, I do see semi-successful creatives in happy marriages. I just have been unable to ever make it work. The men in LA who seemed available for solid relationships with me have tended to be lawyers, engineers, techies, accountants, etc.

  5. Elizabeth Andrews says:

    Oh and my dating has definitely reached the triple digits at this point (never been married, lots of online dating). I can relate!