Should I Ask Out A Hot, Younger Guy? [Ask A Dude]

Hey dude,

I have a nagging problem that I chose to ignore and wish away for a long time now. There is this guy who I worked with at my previous job. I was his team lead and mentor. The thing is I find him insanely attractive, but never asked him out since he is about four years younger. And also because he is very hot and way out of my league. I am quite plain.

I shifted jobs and hoped to forget all about him, but that is just not happening. Should I ask him out and risk being humiliated when he rejects me? Would a very hot guy ever consider going out with a plain girl?

Please reply as soon as you can. I am losing my mind over it.


Troubled Sad Girl

Dear Troubled Sad Girl,

Should you ask out a hottie even though he’s four years younger and you think you’re a nottie? YES! YES! YES!

First of all, the age thing? Take it one day at a time. You won’t know how much of a factor it’s really going to play until you’re a few months into whatever. Even then you can’t be certain. What I can guarantee is that if you think it’s going to be a problem then it will definitely be a problem. So, stop thinking about like that.

Next up, you know who guys think are INSANELY HOT? Slightly older women. Like, for reals FOR REALS! If a man is equally attracted to two women, and he’s, let’s say 25, and one of the women is 23 while the other is 27, the 27 year-old instantly wins. A little age difference like 4 years goes in your pro column. Boom!

You know who else guys think are hot? They’re boss. Or former boss. Oh, sure, a lot of guys want to play the emasculation card (also know as the BS misogynist prick card) but in reality we all want to be a little hot for teacher. Especially a teacher that’s only 4 years difference. I had a teacher freshman year…okay that’s TMI for my readers as this Dude’s identity has to remain kayfabe according to CC rules and regulations. All I’m saying is that the fact that you’re his former boss is another pro in your column.

THIRD! You know what men find super hot? Confidence. As in, the confidence of a woman asking him out. A slightly older former boss with the confidence to ask him out. Do you realize that being asked out is the number 1 fantasy of every guy everywhere? You think we like the pressure? Do you imagine we enjoy sticking our necks out onto the chopping block? No! Just once in our lives we want to be Ted Allen, damn it! Being bold is in your favor, too!

Plus, plain is a matter of perspective. Especially in this circumstance you’ve got a hell of a lot to feel good about. You’re the one in control of the situation. You’re the hot slightly older woman that he probably wondered what “it” would be like while he worked under you. Give yourself permission to have some swag. If you want to give yourself a little more protection then make it a casual ask. Don’t make it a big thing and it won’t be a big thing. I’m telling you, how you approach it is going to affect how he reacts to it. If you ask him out thinking you’ve got 3 strikes against you then he’ll pick up on the negative vibes. If you ask him out for a drink after work to blow off some steam like you’re the one in charge then he’s going leap to attention. Keep it casual and you keep the stakes lower which makes the situation less scary than you might be building it up to be.

Do I think you need to worry about asking this guy out? Hell no! Do I think you should ask him out? OH, HELL YEAH!

And that’s the bottom line,

The Dude

There’s No Such Thing as Being Too Busy [Diary of the Undateable]
There’s No Such Thing as Being Too Busy [Diary of the Undateable]
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