Mrs. Robinson Replies: Five Ways to Handle Messages from Younger Men

Hollywood has long been enamoured of the older woman/younger man romantic scenario, but online dating sites are making it more plausible in the real world. If you’re a woman in your 30s – or 40s, 50s, 60s – you’ve probably received at least one message from a brash young man who wants to get with you. If you’re anything like my clients, you get them all the time. Some are shockingly straightforward, some considered and charming, some unabashedly pleading. How do you respond? Well, that depends on your reaction:

What kind of girl do you think I am?

If you’re not interested in casual sex with anyone of any age, you are well within your rights to ignore messages from randy wannabe boy-toys who are clearly – sometimes vividly – only interested in one thing. If the sender’s date of birth does not place him within your stated age parameters, you are under no obligation to respond at all. If the sender’s not wearing a shirt, and has composed a message of less than ten words or that does not form a complete sentence, delete the original message and just block the young buck. Any reply, even a firm denial of his advances, will only lead to even more insistent and lewd overtures.

You'd be so perfect for my friend/cousin/granddaughter!

If you’re flattered, but not interested, and can detect that a genuine gem of a guy lies behind the gesture, write back. Pleasantly acknowledge the fact that he’s got game – but make it clear that you’re not going to play with him. Just because you’re not buying what he’s selling doesn’t mean he should be taking himself out of circulation, though, and that does sometimes happen to guys who get tired of never receiving replies. (I read a lot of dating profiles. I feel for the fellas sometimes.) Plus, if he really is sincere about wanting to be with an older woman, he might be just right for one of your friends – or your daughter. It’s okay to let him know that it’s nice to be thought of as a viable option by someone of his generation, but you’re looking for someone with a little more mileage.

Sure, I could have babysat you, but there's no harm in writing back

So your interest is piqued by his picture or his prose, but you’ve never dared consider meeting someone in his particular demographic. Depending on the message and your moxie, you can write back taking any number of approaches. Let him know you’re mildly intrigued. (But only mildly.) Or challenge his interest in you directly, if you want to clarify his intentions. You can be as vague or explicit about it as you like. You’re not particularly invested in the exchange, why make it a big deal? You might refer to any number of pop culture touchstones when employing this tactic (“Is this a Graduate/Sex and the City fantasy you’re hoping to play out with me, or do you actually like John Coltrane too?”)

Okay, but this is a one-time deal

There’s nothing wrong with warm-blooded, free-willed individuals of any age getting together to satisfy one of the few truly universal human impulses. Who cares about the psychology behind the message when you haven’t been laid in (please insert whatever you consider a sufficient number of hours/days/months/years to qualify as too long)? There’s no need to be coy, but you don’t have to be crass, either. Reply briefly: “I’d be an idiot to turn down an offer like that, and mama didn’t raise no fool” might do nicely. Just make sure that both parties’ expectations are clearly outlined in subsequent messages. Arrange a brief meeting in a public place beforehand to ensure that he is who he says he is, and that his intentions are what he claims they are. A low-pressure, high-traffic outdoor venue (a park, a city square, outdoor market) is preferable to a sit-down meeting in a coffee shop where you might be spotted by someone either of you knows. You don’t want to have to pass him off as someone you’re mentoring (although that makes an excellent cover if you need one). When arranging intimate encounters, your Spidey Sense needs to be turned up to 11. It’s good practice to avoid traveling in a stranger’s vehicle, particularly if this is just a hook-up.

I'm old enough to be your... girlfriend?

Let’s say you’re willing to consider dating (much) younger men. OkCupid blogger Christian Rudder makes an eloquent case for the older woman/younger man scenario that is well worth reading. Some of the Gen Y types who approach my clients do appear to be sincerely interested in forging a relationship with an older woman. Many write eloquently about it in their messages and their profiles, and why not? Women typically outlive men by 5-6 years. Our more complex sexual responses see us aging differently in the bedroom than our male counterparts (and for us, it’s often more a matter of desire than physiological function). If you’re interested, and you do not discriminate against others on the basis of that which they cannot change, then you owe them the same consideration you’d show anyone else on the site. Don’t write back to the ones who say, “Wow, you’re a total GILF and I want to lick you all over.” But the ones who put real thought into a message – who have obviously read your profile, not just noted your age – deserve a thoughtful, flirtatious reply just like you’d send a chronological contemporary. Thank them for reaching out to you, and answer any questions they ask. Ask some questions of your own. What have you got to lose?

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