The Editors Debate: May-December Relationships

There’s been a handful of high profile older man/teenage female pairings lately and now editors Jennifer Wright and Ashley Cardiff are debating their merits. Are they legitimate? Would having a sugar daddy be great*? (Intern Note: *Yes)

Ashley: Why are you making me begin this? I don’t like beginning things. I like being the rational one. Usually the person who begins does so by spinning the topic in a really off-the-wall direction and tries to set up the opponent for failure by blind-siding her. In this way, the debate begins on a spontaneous, shocking note. And not on a sensible one. Do you know what felching is?

Jennifer: So. I will begin! Give me a second here, since you failed so hard. I think May-December relationships are interesting to us as a society – especially at this point in time – because they seem to point to a reversion to a very traditional kind of relationship. For instance, in the Victorian age people weren’t that OMG SHOCKED that a man in his 40s or 50s might marry a teenager. Because it would be assumed that the man would have to be financially secure enough to provide for a bride, and that would take some time. His being older would also allow him to protect and handle his new wife. This was all seen as pretty normal 100 years ago. But it seems shocking to us now because it is no longer the way relationships work – or the way we like to think of relationships working. At least, I think we’re inclined to WANT to believe that they represent a more equal kind of partnership? But! Is there not something appealing about the idea of being taken care of?

Ashely: You’ve thought about this.

Jennifer: Well, I think it’s interesting that we’ve seen so many recently. The 16 year old singing bride, The McCain staffer, The umm…George Clooney and everyone ever.

Ashley: Oddly, my first instinct is to say, “There’s nothing wrong with liking that security, with being taken care of.” My second instinct is, uh, yes it is. I am not an adult baby. You are not an adult baby.

Jennifer: Huh. That’s interesting. You know, I once wrote an article about Sugar Daddy sites. And I ended up being on there doing INVESTIGATIVE JOURNALISM or something, which I think was an excuse for me wondering if any of these men would actually volunteer to take me away from it all! Because my initial response was “well, I can totally see why this is appealing.” But the moment I talked to any of them I was like “no, no, too icky, no, too icky. Icky, icky, icky.” Why WAS that?

Ashley: Maybe it’s because women actively seeking “sugar daddies” are unable to take care of themselves otherwise, which grosses us out. Or, I guess, if they have a sugar daddy, ultimately, they are.

Jennifer: Clearly.

Ashley: Can we dislike someone for being brazenly parasitic? That’s just an inarguably awful quality in a person, right?

Jennifer: I mean, maybe? I guess what made it disturbing to me was saying “hey, sure, it’s cool if you buy me as you would a piece of furniture” because that contained the implication that I had nothing beyond youth and sexuality to sell. Which is a really sad thought. But I assume we feel differently about marriage, right? I mean, that’s about love.

Ashley: Come on, Jen. We both know that once our youth and sexuality dry up, we’re just gonna be brittle old harpies, swilling gin, complaining about the patriarchy, resenting younger women.

Jennifer: Oh, I can’t WAIT. Can we start now? I’ll get the Tanqueray!

Ashley: Neither of us have shit to offer as far as brains or talent go. We’re women. And we’re in our 20s, which is why successful, attractive, ambitious men over 35 want to date us. Not because we get their pop culture references, that’s for fucking sure.

Jennifer: When they reference Humphrey Bogart I just say “like bogarting a joint?”

Ashley: You say that? “Bogarting a joint?” You meet older men… in 1995?

Jennifer: That’s not something the kids say? I wouldn’t know, I just hang out in old man bars talking about ‘Dark Victory’ or some shit. It’s like no one even remembers Geraldine Fitzgerald anymore! But. I actually wouldn’t judge a woman for wanting a sugar daddy. Seems like hard work! I am not perpetually pleasant in my relationships, and in that sort of thing, you would have to be. I also have felt guilty about when times when men have, say, covered a disproportionate amount of our living arrangements, so I think my temperament would mean I’d be bad at it. As a sugar baby I’m pretty sure you’re not supposed to say “but will you respect me as a partner and, circumstances permitting, potential equal” like, all the time.

Ashley: Being a kept woman is basically about having firm body parts and an agreeable disposition. If you have those, you will be paid in shoes. But don’t be so hard on yourself, Jen. If I were a stock broker, I’d totally pay your rent and take you to trendy restaurants and never go down on you, ever. It’d be great. Being rich is awesome.

Jennifer: I knew a girl who had a sugar daddy once and he just had this open tab for her at various places and it seemed great. SO GREAT. But then I thought about how she kind of had to pretend to like him more than she did. And how incredibly lonely and unbearable it is to even lie in bed with someone you’re not in love with, at least for me. So that is another reason why, while it seems initially appealing, I think it would be a lot more stress than it would be worth. Can we talk about may-December marriages though? Which I think are theoretically different?

Ashley: Oh sure. I think once two people are both adults, age doesn’t really matter. For example, a 10 year gap between a 20 year old girl and a 30 year old man seems to me, vastly more significant than say, the gap between a 30 year old woman and a 45 year old man. Get my meaning?

Jennifer: Sure. But lets talk about like 17 year olds and 35 year olds.

Ashley: Gross!

Jennifer: Oddly, I see nothing odd about the 17 year old in these relationships. When I was 17 I could fall in love with ANYONE.

Ashley: That doesn’t mean you should–

Jennifer: I had no set of criteria. My criteria was pretty much “does this person seem even somewhat cool? Do they like me? We can make it work!” I didn’t have the judgement that comes with a little bit of age. Maybe that’s what makes these girls so appealing to older men.

Ashley: Well, when I was a teenager, a guy in his mid-20s showed an interested in me. I thought it was awesome. He seemed worldly and confident and looked like Cary Elwes. It took me about two weeks of thinking on it to decide I actually found it kind of off-putting. Why weren’t women his age interested in him? Then I heard he’d been trying his luck with another 16 year old a few months before and that made me feel gross. Fortunately for me, I got out of that before I made any bad decisions. I guess I understand being attracted to the physical beauty of a girl in her teens, but I find something about engaging in a romantic relationship with her to be predatory and unsettling.

Jennifer: Me too! A little bit! Too judgey?

Ashley: I think it’s just because I can remember what I liked in a guy as a teenager (namely that he had a car, nice eyes and liked me back) and I think it’s much more valuable, and less traumatic in the end, for teenagers to figure this shit out between themselves. An adult in the relationship seems to indicate, to me, that there’s a developmental problem there. What I’m saying is, of course men want to fuck 16-year-olds. That’s why there are laws against it.

Jennifer: Yeah. If I were a man I’d totally want to date a teenager. They’d be mindlessly forgiving of my flaws. There is no one more open and forgiving than a 17 year old girl who doesn’t really know she’s pretty yet. God, if I were a man, I would be the worst human being you can possibly imagine.

Ashley: That’s really eloquent, Jen. Can I buy you a pair of shoes?

Jennifer: Yes, you may. But! Then how will I ever come into my own as a person, Ashley? I mean, actually, I think it would be okay if you wanted to take over a ton of expenses now. Because YOU’RE A MILLIONAIRE! I’ve kind of evolved past “I’m a whore if a man pays more on shared rent than I do.” But it’s okay, because I have a job and stuff. If you left, I’d be okay even if you wanted to shower me with gifts. That’s the definition of the certain degree of independence that, I think, as modern women we’re told to strive for. I mean, if you became a millionaire and just wanted to take me on spending trips at Christian Louboutin because you got off on that, and it was our sick, mutually enjoyable sex game, then I think I’d be cool with that. But my life would not be in fucking shambles if you left. Which is all I want. And which I’m not sure these girls can have if they marry at 16 or whatever.

Ashley: If I were a rich man in his late forties or early fifties, I’d totally make you my whore if you weren’t such a whore already.

Jennifer: Thank you.

Ashley: You’re so pretty when you agree with me.

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    • Eileen

      Quick question: Why does this website eat my comments so often? Like, I make a comment, and it doesn’t show up. Then I repeat the comment, and it tells me I’ve already posted that, but it still doesn’t show up. Where do the comments go?

      (it’s possible that this is in response to a rant I posted on Jamie’s post about the history of marriage. It’s also possible that marriage and property rights was the topic of the very last term paper I wrote in college, so it’s very possible that this was a LONG rant)

      • Jamie Peck

        Try it again! I would like to read what you have to say.

      • Eileen

        Okay, I’ve tried posting it on just about every post on the site, and it just keeps failing (luckily I’m at the copy-paste point). If you have a Gloss email I can send it there, or…I don’t know, the technology isn’t working :(

      • Jennifer Wright

        I will forward this onto tech, we’ll try do… stuff. Tech stuff.

    • Eileen

      Also, teenagers getting married has always been weird, at least for normal, non-aristocratic women. The average age for an early modern (1450ish-1789) woman to marry was about 25 or 26, same as now, the idea being that the older you were when you married the fewer children you would have. This is actually related to why aristocratic women had wet nurses instead of breastfeeding their own babies – because breastfeeding can keep you from getting pregnant.

      • Jennifer Wright

        Fine! Fine, I was thinking about Edith Wharton. You caught me. Although I guess I generally do think about life among the aristocratic classes because those seem to be the classes that keep the best records (here I was also thinking about one Roman general who taught about how tragic it was that his wife died because she had been so young that she’d been like a daughter to him. I wish I could remember which one. I’m pretty sure it was a letter to Caesar.) But that’s pretty classist of me. Hopefully a rich man will take me up so I can start diary keeping in earnest!

      • Eileen

        If you had led with the Roman general it would have been cooler.

        Also, thank you to tech, although now I look slightly insane posting the same thing multiple times on many posts. I am glad to know that the posts didn’t just disappear ;)

    • M

      Sooo, as someone with an older Sugar Daddy, and as someone who has been into this kind of dating for some time, let me just say that there are many, MANY, types of relationships that can fall under this category. Some of these relationships are downright prostitution/escorting. Some of them are as plain as normal relationships. Some can be loveless, and some have as much love & respect as the healthiest marriages.

      This might come as a shock to you, but you do get to choose the kind of relationship you want. If you want to fuck a guy on a weekly basis for an envelope of cash, you can do that. If you want to accompany a guy on trips and have him buy you shoes, you can do that, too. If you want a normal relationship, with the perks of a Black Amex, that’s an option as well. No one forces anyone to do anything they’re not comfortable with.

      Anyways, I’m into it because the quality of men (IMO) is much higher than in regular dating pools. These guys aren’t loaded by pure chance. They’re kind, intelligent, funny, worldly people who are successful for plenty of reasons.

      As a sidenote, don’t believe all those “Diary of a Sugar Baby” blogs & crap out there. A lot of those are very obviously written by people who work for SD/SB dating sites to glamorize the relationships & pique a girl’s interest.

      • Jennifer Wright

        Want to write about having a sugar daddy? Because I am fascinated by how it works.

      • M

        Sure. Fair warning though, I am a brazenly parasitic adult baby, so I might be hard to work with.

    • Carolyn

      I love the gloss, but I have to say, I NEVER read these debates. They come off as boring at a glance. Maybe it’s a formatting issue I dunno. Maybe if you had clearer distinctions between the editors, or pictures next to each persons text I’d be more likely to read.

      • miinxi

        agreed 100%.

    • A.D.

      I’d rather be the Sugar Mamma…

    • Imogen

      Firstly, I love these debates. Someone earlier has said they’re boring, I def disagree.
      Secondly, I am currently seeing someone who is 10 yrs older than me. (I am 24 and he is 34.) Not sure if this counts as a May to Dec, I wldnt count it as one, but it is the biggest age difference I have ever been in and taken seriously and there is a big difference in income (ie, I have none).
      And its pretty good thus far. The beginning of a normal remationship, where we split the prices in a logical way (ie favourable to me), but make joint decisions, respect each other, act as adults and have great sex.

    • Alessia

      These “Editors Debates” absolutely make my life. Please, never stop.