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This week’s dilemma:

You and your best friend are both in your forties. You’ve grown up together, and you’ve also watched her two sons grow up. You even used to babysit for them, when their parents needed a break.

The eldest, (Let’s call him Ryan, shall we?) is now twenty-five years old, and lately, you’ve been looking at him differently. You also sense that he’s attracted to you.

One day he tells you that he finds you hot, and would like to date you.

You’re very flattered, but although you also find him attractive, you can’t help but think about his mother’s reaction.

What do you do? Do you honour the friendship and leave Ryan be, or do you date the young hot stud, and worry about the consequences later?

24 Comments »

  • While I don’t have an issue with age-discrepant relationships as a general rule (I’m actually in one myself)… it would be more than a little squicky to date someone I baby-sat since they were in diapers. It’d be one thing if it had been someone I had not known that long, but that just makes it too close to incest for me, even if it technically isn’t.

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  • Nonny said it perfectly. I helped raise my godson and I would probably look at him as if he’d lost his mind if he said something like that to me. Especially since he’d me momma.

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  • Marianne McA
    April 3
    10:42 am

    No: Nonny said it exactly right, it would feel a little incestuous. I think the children who are in your house frequently through the years become sort of pseudo-children – I couldn’t make that mental leap.

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  • SarahT
    April 3
    1:13 pm

    I think I would feel flattered but leave it at that. Aside from the weirdness of having changed his nappies, I wouldn’t want to risk my friendship with his mother. No matter how hot Ryan might be, it’s not likely to be more than a fling. If I thought he was destined to be my one true love, that would be a different story entirely.

    Speaking of which, wasn’t Barbara Windsor’s husband the son of a friend? I think he’s something like 30 years her junior.

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  • Nonny summed it up. Flattering but anyone you knew as a child is just over the line.

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  • M E 2
    April 3
    1:43 pm

    Ewwwwwww ……. Hell NO!

    And that applies even if I hadn’t known him as a child/his mom is my best friend/etc.

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  • Anon76
    April 3
    3:01 pm

    Nonny nailed it on the head for me.

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  • Um…no. Again, Nonny nailed it.

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  • Ew, no way.
    I’m like an aunt to my best friends kids. The thoughts of doing anything sexual with them, even if they are over 18, is disgusting.

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  • Parth-Anon
    April 3
    5:02 pm

    I wouldn’t do it even if I wanted to, because of the stress it would put on Ryan’s mother and our relationship.

    I would try and talk to her about it though, and see what she thinks. If his family’s cool with it, then why not? If I myself am attracted to him and don’t see him as a child of mine, then I see no ethical problem here.

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  • oh god no…just weird and wrong

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  • Randi
    April 3
    6:51 pm

    I’m an agist (sorry- I just don’t date men who are younger than I am) so he would qualify as an automatic no.

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  • Dittoing Nonny.

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  • FD
    April 4
    1:28 am

    That would be a no. Not because of the age discrepancy, there’s too much of an emotional power differential, given the practically-helped-raise-him thing, and then there’s the very likely torpedoing a forty year friendship part.

    Thank him nicely, enjoy the ego boost, and move on.

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  • Nope – it’s not the age thing though I think that would be a bit too much of a difference – it’s the close friend – known him since he was a kid thing. Though I would be HIGHLY flattered it he thought I was hot šŸ™‚

    Interestingly – my 20 year old son is dating someone six years older than he is. He thought it would bother me – but it doesn’t at all. But if she were 20 years older – I would have second thoughts about it šŸ™‚

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  • No way….there is too much at stake (friendship) and just the thought of one of my friends dating my son makes me want to throw up.

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  • I wanna buck the trend.
    I would date the dude.

    Yeah right. Umm, no. There’s just too much ick to wade through.

    On the other hand, if in true romance fashion we were stranded on a desert island somewhere together and his folks had just died and we found ourselves bound together in a moment of intense, shared grief… still no.

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  • Definitely a no. And I wouldn’t be able to give a thumbs up to a novel with this sort of plot either…although if he turned out to be a stalker and her rejection put him over the edge…yeah I could dig that sort of novel.

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  • No way. Women throw other women under the bus too often for men. The friendship should come first. And it’s squicky, too.

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  • Jane Austen’s Emma pretty much had the same premise, though, but in reverse. Hmm, interesting, isn’t it?

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  • I note that the majority of you have said , no way, no how, but I personally think that if the above scenario actually happened, the percentage who wouldn’t date him would reduce exponentially.

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  • I have a son who’s turning 21 in a few months, Karen–no way I can look at a kid barely four years older and get a sex vibe.

    Gah!

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  • Lorraine
    April 9
    2:21 am

    Hot young studs are a dime a dozen *at least in theory*, but a lifelong best friend only comes around once. I’d never risk her friendship for a fling, and I’d never allow myself to think it could be anything more.

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  • Jen
    April 9
    9:32 pm

    No way. Nonny said it best. I’m not opposed to older woman/younger man relationships, but in that kind of close-as-family situation, I’d be more inclined to believe it was either a crush, or some other social thing the young man was trying to work through. There’s probably something there that says he feels comfortable enough with you as a family friend to confess something that potentially awkward. So even though there’d be no dating or hanky-panky going on, I’d still apply Dan Savage’s Campsite Rule and let him down gently and with respect. And possibly in private, swearing-unto-secrecy, giving my friend at least a heads-up over it if the situation merited it.

    I wouldn’t ever consider it, yet somehow if the situation were the plot of a romance novel, I’d be interested to see how the author would sell it, and if the author would be able to pull it off or not.

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