How should I proposition my co-worker?
March 4, 2010 5:43 PM   Subscribe

Self-love is great, but it's getting a little old. How should I proposition my co-worker...?

Me - 24 year old female. Broke up with my boyfriend of two years a month ago and I am doing great. However, I'm starting to get the itch. I'm looking for a very casual relationship..

Him - 19 year old male, let's call him S. Also got out of an LTR about 2 months ago. We flirt and get along well but aren't particularly close friends. I'm very physically attracted to him.

S and I work about once a week together at a very casual, cool, restaurant, with a bunch of other young folk. Inter-employee hookups are definitely not unheard of.

If it were anyone else, I would simply ask S (while we were leaving for the night) if he wanted to get a drink. However, he's not yet 21 so that's out of the question. We also live about 40 minutes away from each other, both in very rural areas (no coffeeshops or anything) with work smack dab in the middle.

Also, I'm not trying to be cocky but I have been told that I'm pretty physically slamming (attractiveness-wise). Of course, different strokes for different folks and all, but I'm no toad.

I kind of just want to bluntly say "If you're looking for a good time call me. You are the hotness." But, ya know, without the cliche-corniness. I'd definitely be able to take it if he rebuffed me, as we aren't best friends and only work together once a week. There's other fish in the sea.

How should I go about this?
posted by anonymous to Human Relations (22 answers total) 3 users marked this as a favorite
 
It seems like it's a problem of logistics more than anything else. Say he was 21 years old, where would you go to hook up anyway?

Perhaps there is a hotel near your workplace with a restaurant. You could invite him out for dessert or something in the restaurant of the hotel, and then you could go get a room.

If there is no hotel, then you still have to find a place to hook up, so it looks like you have to invite him back to your place. You could be totally blunt and say at the end of your shift "I want you to come back to my place."

However, he might have soccer practice or something the following day, so it might be best to plan it out. You could flirt with him during one shift and at the end of the shift ask he has any plans after work the following week. Then you say "come back to my place next week. Bring a toothbrush."

But just be direct. Love (or, in this case, lust) will find a way.
posted by KokuRyu at 5:50 PM on March 4, 2010


Yup - be direct. "How about dinner at my place? Bring a toothbrush & a change of clothes."
posted by torquemaniac at 5:58 PM on March 4, 2010 [3 favorites]


Don't sweat age diff. I am 29 years older than my wife.we in our 26th year of marriage. Yes...bars an issue for him. Go for what you want.
posted by Postroad at 6:20 PM on March 4, 2010 [3 favorites]


A 19 year old guy will be thrilled to be pursued by a 24 year old.
posted by dfriedman at 6:23 PM on March 4, 2010 [1 favorite]


If you think you are attractive, you are attractive. If you hit on your coworker, he will not think it is creepy.

I remember at that age that it was a little unsettling to be hit on by late-30s women at the bar, but anything younger than that was fine by me.
posted by KokuRyu at 6:31 PM on March 4, 2010


Pretty much an any year old guy would be thrilled to be pursued by a 24 year old woman.

"Hey, let's get a drink?"

"Eh? Hmm. The thing is I'll probably get carded."

"Not a problem. I've got a bottle of wine and a picnic basket. Let's go."

Also, Postroad: I need a bigger calculator to figure out a 29 year age difference and 26 years of marriage.
posted by notyou at 6:33 PM on March 4, 2010


Postroad is an older gentleman.

But yeah, I'd just ask him out. If you don't already have his digits, I'd start there. Then text and ask him to come by sometime this weekend/whenever for some drinks. He'll get the idea.
posted by PhoBWanKenobi at 6:42 PM on March 4, 2010


I say invite him to get a drink with you. At your house.
Talk, listen to some music, have a decent sort of cool movie to watch, and if there's chemistry there then go for it. If not then just have a fun drunken silly time and let him fall asleep on your couch. I've been in this situation at times (on one occasion she poured half a bottle of wine in a cup for me and then put an Iranian movie on without subtitles), and it's very forward while still being friendly and un-reproachable. If he says he has something to do and can't make it then see if you can make plans for a night you're both free, if he dodges that then you can just drop it without being embarrassed.
posted by JackarypQQ at 7:16 PM on March 4, 2010


Any 19 year old is still coming off of the hormonal stage of life. Even if you were fat and ugly (JUST STATING A POINT! I MEAN NO HATE) he probably would still tap you no matter how you approach it.

Not sure how much time you could get to talk to him at any given time, you could always stumble on the subject and just be like "you know, ive been pretty lonely lately" and give him that look. It will all roll from there.
posted by NotSoSiniSter at 7:20 PM on March 4, 2010


Having once been a 19-year old guy, being propositioned in any way, shape or form by a "no toad"-ish female would be a huge cause for celebration. Don't sweat the details. :)
posted by zachawry at 7:26 PM on March 4, 2010


19-year-old? I'd think you could just flat out ask him. The guys I hung out with at that age were not interested in finesse.
posted by runningwithscissors at 7:47 PM on March 4, 2010 [1 favorite]


I believe you are overthinking this and I agree that a direct question will likely be met with stunned disbelief followed by acceptance followed by him doing the happy dance once he is alone.
posted by Justinian at 9:19 PM on March 4, 2010


I did exactly this (right down to the ages) & we've been married now for the last 15 or so years (no, for the first six months it was just a "convenient hookup"). Heh.

Have a good time!
posted by susanbeeswax at 10:51 PM on March 4, 2010 [1 favorite]


Oh yeah -- the first night he turned me down because he didn't believe it. I said, well, think about it. And he came shuffling back the next day at work and said 'I've reconsidered your offer, would you like to see a movie tonight at my place?' 19 -- pretty much enough said.
posted by susanbeeswax at 10:53 PM on March 4, 2010


Broke up with my boyfriend of two years a month ago and I am doing great.

What's the rush? Hooking up with someone five years younger than you seems unwise.
posted by Carol Anne at 6:12 AM on March 5, 2010 [1 favorite]


Hooking up with someone five years younger than you seems unwise.

Or... fun.
posted by beerbajay at 6:50 AM on March 5, 2010 [2 favorites]


He might be crazy and want more and you might anger him by falling in love with someone else and stopping what you do with him. 19 yr olds are unpredictable.
posted by anniecat at 7:52 AM on March 5, 2010 [1 favorite]


Here's a little trick that will work for a 19-year-old guy, or a guy at any age for that matter if the woman is attractive and confident:

You walk up to him, look him right in the eyes, and say, "I really want to have sex with you, do you want to come over to my place after work?" Having a woman do that is every man's dream and so few of us ever get to experience it. It happened to me once. She said, "Look, I think you're hot and I need to have sex tonight, so do you wanna come home with me?" I nearly shat. I had to politely decline because I wasn't single at the time, but that doesn't mean it wasn't one of the most confidence-boosting, flattering, most awesome things I've ever experienced.
posted by fso at 8:25 AM on March 5, 2010 [1 favorite]


He might be crazy and want more and you might anger him by falling in love with someone else and stopping what you do with him. 19 yr olds are unpredictable.

I think that's a little overboard. Notice all the "might"s in the sentence. I think you're in the clear here if you know and trust him.
posted by runningwithscissors at 9:14 AM on March 5, 2010


What's the rush? Hooking up with someone five years younger than you seems unwise.

As someone who's boyfriend is 16 years younger than herself, I find that wildly amusing.

19 yr olds are unpredictable.

uh....way to generalize.

I think you're golden. No advice on how to proceed, but...have fun!
posted by noxetlux at 9:27 AM on March 5, 2010


"Do you need a ride back to my place?" never. fails.
posted by WeekendJen at 1:25 PM on March 5, 2010


I think as long as you don't just say, "Hey, wanna bone?" it wouldn't be sexual harassment if you both work part-time in a restaurant and you have no control over his employment. I'm not saying this from a legal standpoint, but from a having been a young person working in a restaurant standpoint. I think the best way to go about it is to just ask him out on a date. Like, "Hey would you like to go [insert activity here, like movie, dinner, a party, whatever]?" This gives him an out to say no if he's uncomfortable, and you haven't done anything overtly sexual. You just innocently invited him out.

I have a feeling he'll be down. Unless he's gay or has a preference for girls who look nothing like you regardless of your objective attractiveness.
posted by ishotjr at 7:28 PM on March 5, 2010


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