How To Approach the Much Younger Man

To borrow a line from Kaci, so there’s this boy. A totally different situation but a boy nonetheless. The boy in question is one I happened to work with. He’s new to our school this year and, well, new to teaching making him 23. Yep, 23. But he’s also hot and there is a big part of me that wants to go out on a huge limb and try to find out if he would be interested in me.

Now, I know there will be many of you, Kira included, who will give me hell here, but I suppose that is a risk I’m willing to take. Most of you already know that I prefer to date younger men. I’ve dated them this much younger before. The difference is all of them approached me.

So, the problem is I just very simply have no idea how to approach. For a woman so much older than the man she is interested in there is a huge risk. That risk is the “ewwww factor.” There’s always a chance that he’ll take one look, realize you’re old enough to be his mom and say, “Ewwwwwwwwww!”

It’s very different when a much younger man approaches an older women. An older woman will likely be flattered even if she’s not interested. Thus, it seems that the thing to do is find a way to express interest in a way that will encourage him to approach rather than straight out approaching him. I just have no idea how to do that.

In a typical work environment, it might be different. It might even be different in a different school, but the way ours is set up, our paths just don’t often cross. Once in awhile I run into him in the workroom. In the past he has come to my classroom to discuss a few students we have in common, but that’s unlikely to happen now since my bilingual assistant is going to his class with those kids.

I’m a little afraid of setting up situations to run into him. It would be difficult to do and might be too obvious. Or is too obvious a bad thing? Ugh!

Thoughts? Ideas? Suggestions?

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Posted by lisaq on Sunday, October 5th, 2008 and is filed under Featured. You can follow any responses to this entry through the RSS 2.0 feed. You can leave a response, or trackback from your own site.

9 Responses to “How To Approach the Much Younger Man”

Meghan October 5th, 2008, 12:13 pm

Are you even allowed to approach him seeing as you are at the same school? That’s the part I would wonder about being cloudy. Or is it totally laid back and no worries about the whole ‘conduct’ thing?

I just recently told a girlfriend…’Don’t get your meat where you get your bread!’

What a phrase!
lisaq October 5th, 2008, 4:40 pm

It actually happens on a pretty regular basis in our school Meghan. Teachers hook up all the time. I think, if handled correctly, it will be just fine.
saneandsingle October 5th, 2008, 9:56 pm

I need to work in your school! There are no men even remotely attractive at mine. Hell, everyone there is married anyway! Ugh.

Check to see if he has a myspace account and do a little flirting there first!
lisaq October 6th, 2008, 6:07 am

Haha…we do have some eye candy sane and single. I actually thought of the myspace thing. He hasn’t logged on there since January though, so don’t know how effective that would be.
auntiegwen October 6th, 2008, 11:17 am

Step away from the pretty boy

I repeat

Step away from the pretty boy

I know some men date older women but how do you know he’s one ? and he may not be mature enough to be grateful for the great compliment that your interest is.

I just couldn’t do it at work, I have 2 teachers who are very keen on me but the thought of seeing them in the staff room day after day makes me keep my distance.

auntiegwen´s last blog post..I’ve lost it
lisaq October 6th, 2008, 8:38 pm

Haha Gwen! I don’t. It’s why I’m not sure how to approach. Though I’m comfortable dating younger men, I’ve never approached this young before…though I have had them approach me. I posted the same question on ageless love’s forum and got back some pretty decent suggestions. I’m still weighing it out though. We’ll see.

The work thing doesn’t bother me really. Happens all the time in our school. Hell, one of the couples that started dating a couple of years ago is now engaged. Besides, where the hell else am I going to meet anyone? I’m so busy, I’m either there or at home. Feels like in order for me to meet someone, they’d have to be airdropped onto my front porch!
cassie November 18th, 2008, 6:01 pm

Be nice to him. Smile. Flirt just a little and then stand back. A guy his age (heck most guys) are quite visually aware, so stimulate interest by being dressed in a way that makes you feel sexy (but don’t go for the slutty look!). Be your usual relaxed and confident self. If he’s a nice guy, let him see you like him and give him the opportunity to get to know you on a friendship basis first. (Save the lust for later!!). And good luck!
lisaq November 20th, 2008, 6:47 am

Great suggestions Cassie! Thanks!
George March 25th, 2009, 10:21 am

I’ve never given this a try, but I think it’s about time I do.