How do I ask out the intern without embarrassing myself or her?
June 3, 2009 11:02 AM Subscribe
Dating/Work Filter: There is an intern who just started working at a company I freelance at, who I find very attractive. We just randomly met on the elevator today and engaged in some small talk, and I have no necessary direct contact with her, or sit in her area. What's the best way to go about asking her out?
Basically, I don't have the balls to just walk over to her area and say "hey, do you want to go out some time?" One, I don't want to risk any humiliation in front of co-workers. Two, I don't want to put her in an awkward situation. One bonus is her boss is an acquaintance of mine outside of work. I'm wondering if I can play that to my advantage.
Any suggestions on how to go about this?
Basically, I don't have the balls to just walk over to her area and say "hey, do you want to go out some time?" One, I don't want to risk any humiliation in front of co-workers. Two, I don't want to put her in an awkward situation. One bonus is her boss is an acquaintance of mine outside of work. I'm wondering if I can play that to my advantage.
Any suggestions on how to go about this?
Do you know for sure your company doesn't have a policy on inter-office dating? Also, are you sure you're not going to have any professional relationship with her whatsoever in the future?
Oh, whatever you do, don't use company email to do it.
posted by jerseygirl at 11:09 AM on June 3, 2009
Oh, whatever you do, don't use company email to do it.
posted by jerseygirl at 11:09 AM on June 3, 2009
Send her a very diplomatic email, explaining what you said in your post, that you do not want this to be discomforting to her, etc, but would you like to go out sometime? Then, avoid initiating contact for awhile to give her space to process.
If she does not want to, it'll feel shitty no matter what form your asking takes.
Good luck!
posted by Danf at 11:09 AM on June 3, 2009
If she does not want to, it'll feel shitty no matter what form your asking takes.
Good luck!
posted by Danf at 11:09 AM on June 3, 2009
Aside from the above questions, just start with trying to be work friends with her first and build from there.
posted by jerseygirl at 11:09 AM on June 3, 2009 [2 favorites]
posted by jerseygirl at 11:09 AM on June 3, 2009 [2 favorites]
Yeah. Don't.
She's an intern, her boss is a friend of yours and you seriously are thinking of asking her out? Seriously?
Really?
I think it would behoove you to stop for a moment and consider the dynamics of the situation.
Either she accepts or she does not. If she accepts and then decides she doesn't want to go out with you again, at best this makes things uncomfortable between the two of you and puts her boss in an impossible bind (friendship or work relationship with his report).
If she accepts and decides that she wants to date you this puts her, her boss and you in an uneasy relationship with the rest of the company.
If she declines, you look the fool, she feels uncomfortable and you stick her boss, your friend, into the middle of an unpleasant situation.
Surely there are other fish in the sea who do not present problems such as these.
posted by dfriedman at 11:10 AM on June 3, 2009 [17 favorites]
She's an intern, her boss is a friend of yours and you seriously are thinking of asking her out? Seriously?
Really?
I think it would behoove you to stop for a moment and consider the dynamics of the situation.
Either she accepts or she does not. If she accepts and then decides she doesn't want to go out with you again, at best this makes things uncomfortable between the two of you and puts her boss in an impossible bind (friendship or work relationship with his report).
If she accepts and decides that she wants to date you this puts her, her boss and you in an uneasy relationship with the rest of the company.
If she declines, you look the fool, she feels uncomfortable and you stick her boss, your friend, into the middle of an unpleasant situation.
Surely there are other fish in the sea who do not present problems such as these.
posted by dfriedman at 11:10 AM on June 3, 2009 [17 favorites]
One bonus is her boss is an acquaintance of mine outside of work. I'm wondering if I can play that to my advantage.
Are you kidding me? Assuming you're not being trolling or being disingenuous, you are really coming across as a grade A dipshit here, to be perfectly honest. Have at least a modicum of professionalism and just don't go there.
posted by dhammond at 11:13 AM on June 3, 2009 [19 favorites]
Are you kidding me? Assuming you're not being trolling or being disingenuous, you are really coming across as a grade A dipshit here, to be perfectly honest. Have at least a modicum of professionalism and just don't go there.
posted by dhammond at 11:13 AM on June 3, 2009 [19 favorites]
Seconding the work-friends-first suggestion, too. She might find it awkward and off-putting if you immediately express such direct attraction, whereas lunches and casual conversation will let her feel more at ease. Don't jump the gun.
posted by Bakuun at 11:14 AM on June 3, 2009
posted by Bakuun at 11:14 AM on June 3, 2009
She's an intern -- presumably this is a limited engagement. Wait until she's done.
posted by crickets at 11:15 AM on June 3, 2009 [3 favorites]
posted by crickets at 11:15 AM on June 3, 2009 [3 favorites]
Ugh scattered day-before-vacation brain today. Another thing, companies can be really weird about the lines on any kind of harassment. Someone I know started emailing a girl at work he was somewhat interested in, and I don't know how far he went with it, but it ended with her feeling weirded out by him contacting her, and he being terminated.
You mentioned you're freelancing. Earlier AskMes have you looking for temp work. That's a small world. You don't want to do anything to compromise what I presume is a very good professional reputation.
posted by jerseygirl at 11:18 AM on June 3, 2009
You mentioned you're freelancing. Earlier AskMes have you looking for temp work. That's a small world. You don't want to do anything to compromise what I presume is a very good professional reputation.
posted by jerseygirl at 11:18 AM on June 3, 2009
I'd say go for it.....just invite her out in a friendly manner for lunch or after drinks...not as a date and try to see her response and where to take it from there....you only live once....
posted by The1andonly at 11:20 AM on June 3, 2009
posted by The1andonly at 11:20 AM on June 3, 2009
If she's attractive youre not the first guy ever to ask her out. Let her know you are interested in getting to know her more (i.e. lunch) and she will handle it from there. I highly doubt doing this will result in humiliation in front of your coworkers.
posted by norabarnacl3 at 11:21 AM on June 3, 2009
posted by norabarnacl3 at 11:21 AM on June 3, 2009
I don't think you\we know enough to think about asking her out.
First - what's your companies policy?
Second - bad idea if you are in any sort of position with having power over her.
Third - You always want to know if the person at work is involved with someone else before asking them out. I'd say you have a 99% chance of failure if she has a boyfriend.
I agree with others that your best bet it to somehow time asking her to lunch in a friendly way.
posted by zephyr_words at 11:22 AM on June 3, 2009
First - what's your companies policy?
Second - bad idea if you are in any sort of position with having power over her.
Third - You always want to know if the person at work is involved with someone else before asking them out. I'd say you have a 99% chance of failure if she has a boyfriend.
I agree with others that your best bet it to somehow time asking her to lunch in a friendly way.
posted by zephyr_words at 11:22 AM on June 3, 2009
Have to say I'm with dfriedman on this one. There are plenty of easy, friendly, non-threatening ways for you to ask her out. Problem is, there is no easy, non-career-sabotaging way for her to turn you down. Also, even if she is interested in you and would want to say yes, this is an internship - an experience that's supposed to be about learning, not about dating upper-level coworkers. Not to mention, dating someone when she's that new at a company could easily earn her the "Sally-the-Slutty-Intern" label. You sound like a nice guy. I don't think you'd want to do that to her.
When she's finished her internship and is leaving the company, tell her that you think she's an intelligent, attractive woman, and offer to take her out for a drink sometime if she's interested.
posted by philotes at 11:24 AM on June 3, 2009 [1 favorite]
When she's finished her internship and is leaving the company, tell her that you think she's an intelligent, attractive woman, and offer to take her out for a drink sometime if she's interested.
posted by philotes at 11:24 AM on June 3, 2009 [1 favorite]
Thanks for the suggestions so far. I should elaborate on a couple things:
As far as inter-office dating rules go, it's very lax here. I work for a television cable company, and know a handful of couples who have met here.
As I said, we work in completely different worlds though we work for the same company. So I'm not very concerned about the professional connections aspect.
I suppose I'll just drop by where she sits and ask her if she wants to grab lunch.
posted by helios410 at 11:26 AM on June 3, 2009
As far as inter-office dating rules go, it's very lax here. I work for a television cable company, and know a handful of couples who have met here.
As I said, we work in completely different worlds though we work for the same company. So I'm not very concerned about the professional connections aspect.
I suppose I'll just drop by where she sits and ask her if she wants to grab lunch.
posted by helios410 at 11:26 AM on June 3, 2009
Best answer: Yeah, I'm disagreeing with the "whatever you do, don't make eye contact SEXUAL HARRASSMENT OMG" people. Email her to say "Hey, just wanted to welcome you to the company. If you'd like someone to grab lunch with, I'm free."
Keep it to lunch, gauge interest there, move forward accordingly. It's her career; if the intern thing is an issue, it's her responsibility to simply say no. Don't "play up" the boss thing at all, no matter how you meant that. And confirm your employer's policy on intra-office dating.
posted by disillusioned at 11:32 AM on June 3, 2009
Keep it to lunch, gauge interest there, move forward accordingly. It's her career; if the intern thing is an issue, it's her responsibility to simply say no. Don't "play up" the boss thing at all, no matter how you meant that. And confirm your employer's policy on intra-office dating.
posted by disillusioned at 11:32 AM on June 3, 2009
On preview, everything you said. :p
posted by disillusioned at 11:32 AM on June 3, 2009
posted by disillusioned at 11:32 AM on June 3, 2009
I'd say strike up a rapport with her. Maybe go say hi to her boss and say hello to her as well while you're over there. You mention she's attractive, but not whether she's responsive in a positive way to you. If it seems like she might be interested, see if she wants to grab lunch sometime.
posted by mattsweaters at 11:42 AM on June 3, 2009
posted by mattsweaters at 11:42 AM on June 3, 2009
First, don't use email for this. Company or personal. Period.
Second, asking to lunch sounds like a good first step. Even with a group is fine, if it goes well, then ask her out on your own.
Third, don't pass up an opportunity to meet someone new. Dating or otherwise.
posted by shinynewnick at 11:46 AM on June 3, 2009
Second, asking to lunch sounds like a good first step. Even with a group is fine, if it goes well, then ask her out on your own.
Third, don't pass up an opportunity to meet someone new. Dating or otherwise.
posted by shinynewnick at 11:46 AM on June 3, 2009
One bonus is her boss is an acquaintance of mine outside of work. I'm wondering if I can play that to my advantage.
No, that's actually not a bonus. I'd completely avoid mentioning it, because it's a card you don't even want her thinking is in your deck, and it's definitely not a card you should play.
Apart from that, just decide to run into her when she's not around her co-workers, tell her about the fun place you're going to lunch tomorrow-- describe its charms at length and in enthusiastic detail--, and invite her to come along.
posted by darth_tedious at 11:59 AM on June 3, 2009
No, that's actually not a bonus. I'd completely avoid mentioning it, because it's a card you don't even want her thinking is in your deck, and it's definitely not a card you should play.
Apart from that, just decide to run into her when she's not around her co-workers, tell her about the fun place you're going to lunch tomorrow-- describe its charms at length and in enthusiastic detail--, and invite her to come along.
posted by darth_tedious at 11:59 AM on June 3, 2009
See if she's on Facebook. If so, add her as a friend, perhaps with some inane question in your friend request message. Once you are Facebook friends, you'll know something about each other, and you can more safely ask her to do something she might actually be interested in, rather than being just another guy asking her out to dinner/coffee.
posted by coolguymichael at 11:59 AM on June 3, 2009
posted by coolguymichael at 11:59 AM on June 3, 2009
Modern dating has an element of The Battle of Who Could Care Less. "Interest" is now perceived as creepy. About as close as I get to asking anyone right out is "going to a thing."
Example 1: She's leaving in a week. An art exhibit of mutual interest is coming. You are going to go see it Thursday. You let her know that you are going to go there. Maybe you will see her there. Too interested: giving her a wall calendar of that art.
Example 2: She's leaving in a week. A local band, which maybe you both like, is playing at a bar down the street. You'll be there Tuesday night. Tell her that they're playing in town and you're going. Maybe you will see her there. Too interested: making her a CD of that band, buying her a ticket.
This rather sideways approach has a few things to recommend it:
1) Plausible deniability. This has both legal and face-saving advantages.
2) Somewhere along the line, any level of interest greater than a Botoxed, expressionless mask of apathy was translated into "stalker." So, this is almost the barest expression of interest you can manage.
3) Subtlety is all. Some women find the direct ask-out puts them on the spot. If she shows up, that is a signal you can step that up to a farewell luncheon, on you. It's on you because she's an intern and is probably not paid well, not because it is a date. After that, you can step it up by giving her your card with your phone number on back. "Call me if you need references, or just to talk."
You can do this precisely twice. The first time, she might be busy. After the second time of her not showing up, sure, it's in the realm of possibility that she's busy both times, but it is more likely that she is disinterested.
The problem in your specific case is that, aside from the smallest of talk, you have nothing established in common, besides where you two work and that the majority of your DNA is similar, the latter of which you happen to share with the rest of the human race. So, before you do the "going to a thing" thing, talk with her. And I mean talk with her, as opposed to other prepositions, such as "to," but most especially "at."
posted by adipocere at 12:05 PM on June 3, 2009 [12 favorites]
Example 1: She's leaving in a week. An art exhibit of mutual interest is coming. You are going to go see it Thursday. You let her know that you are going to go there. Maybe you will see her there. Too interested: giving her a wall calendar of that art.
Example 2: She's leaving in a week. A local band, which maybe you both like, is playing at a bar down the street. You'll be there Tuesday night. Tell her that they're playing in town and you're going. Maybe you will see her there. Too interested: making her a CD of that band, buying her a ticket.
This rather sideways approach has a few things to recommend it:
1) Plausible deniability. This has both legal and face-saving advantages.
2) Somewhere along the line, any level of interest greater than a Botoxed, expressionless mask of apathy was translated into "stalker." So, this is almost the barest expression of interest you can manage.
3) Subtlety is all. Some women find the direct ask-out puts them on the spot. If she shows up, that is a signal you can step that up to a farewell luncheon, on you. It's on you because she's an intern and is probably not paid well, not because it is a date. After that, you can step it up by giving her your card with your phone number on back. "Call me if you need references, or just to talk."
You can do this precisely twice. The first time, she might be busy. After the second time of her not showing up, sure, it's in the realm of possibility that she's busy both times, but it is more likely that she is disinterested.
The problem in your specific case is that, aside from the smallest of talk, you have nothing established in common, besides where you two work and that the majority of your DNA is similar, the latter of which you happen to share with the rest of the human race. So, before you do the "going to a thing" thing, talk with her. And I mean talk with her, as opposed to other prepositions, such as "to," but most especially "at."
posted by adipocere at 12:05 PM on June 3, 2009 [12 favorites]
See if she's on Facebook. If so, add her as a friend
Awful advice. You barely know her so don't do this. Ask her to a casual lunch and learn more about her. For all you know she might be taken. If she is, and she senses your interest in her, she will make sure you know. Nothing is lost here, no embarrassment, and you have a new friend to eat lunch with.
Otherwise keep the conversation going. As you chat with her you'll find out more about here interests, what kind of music she likes etc, giving you a better idea of what to propose as a date. Soon enough you'll find out if she's interested in you too, and you can take it from there.
posted by special-k at 12:13 PM on June 3, 2009
Awful advice. You barely know her so don't do this. Ask her to a casual lunch and learn more about her. For all you know she might be taken. If she is, and she senses your interest in her, she will make sure you know. Nothing is lost here, no embarrassment, and you have a new friend to eat lunch with.
Otherwise keep the conversation going. As you chat with her you'll find out more about here interests, what kind of music she likes etc, giving you a better idea of what to propose as a date. Soon enough you'll find out if she's interested in you too, and you can take it from there.
posted by special-k at 12:13 PM on June 3, 2009
Best answer: Man, what is the big deal? Direct is the best approach. Not email, not any other indirect means. Leave the door wide open for her to walk out on you so that she does not feel trapped. Just go strike up an idle conversation, see how it goes, and if the two of you have chemistry, ask her out.
posted by randomstriker at 12:44 PM on June 3, 2009 [1 favorite]
posted by randomstriker at 12:44 PM on June 3, 2009 [1 favorite]
great post adipocere but never forget that how caught up someone is in social posturing is always an individual choice.
posted by stratastar at 1:16 PM on June 3, 2009 [1 favorite]
posted by stratastar at 1:16 PM on June 3, 2009 [1 favorite]
Just flat out get the balls to do it. That's what women want anyway.
posted by Ironmouth at 1:25 PM on June 3, 2009 [1 favorite]
posted by Ironmouth at 1:25 PM on June 3, 2009 [1 favorite]
Do it. It could be that this great looking girl is tired of being alone. Everyone assumes that she must have a line of fellows that she can call anytime, so few make an approach.
If she laughs at you, and turns away, then you have been shot down. You can recover. It is still better than never trying at all.
posted by Midnight Skulker at 1:41 PM on June 3, 2009
If she laughs at you, and turns away, then you have been shot down. You can recover. It is still better than never trying at all.
posted by Midnight Skulker at 1:41 PM on June 3, 2009
I wouldn't worry about all the warnings about dating an intern, etc.
If she would recognize your name from an email, you can send out an email to a small group 3-4 people and include her on it, inviting her to lunch or happy hour or something. If she's interested she'll either go, or say she can't make it but to invite her next time, and hopefully one of those times she'll come out and you can feel out the vibe in person. Then it's not as ask-outy when you ask her to hang out again.
Definitely don't ask her out over email, only group outings are OK over email. If she wouldn't recognize your name right away from seeing an email from you then maybe keep trying to bump into her in the elevator or somewhere. Maybe one of those times say "hey a bunch of us are going out for happy hour after work, you want to come? Give me your # I'll text you the details" and then round up your friends and MAKE them go out after work - it'd be too weird if all of a sudden you were like, "oh, people cancelled, do you still want to go?"
posted by KateHasQuestions at 2:38 PM on June 3, 2009 [1 favorite]
If she would recognize your name from an email, you can send out an email to a small group 3-4 people and include her on it, inviting her to lunch or happy hour or something. If she's interested she'll either go, or say she can't make it but to invite her next time, and hopefully one of those times she'll come out and you can feel out the vibe in person. Then it's not as ask-outy when you ask her to hang out again.
Definitely don't ask her out over email, only group outings are OK over email. If she wouldn't recognize your name right away from seeing an email from you then maybe keep trying to bump into her in the elevator or somewhere. Maybe one of those times say "hey a bunch of us are going out for happy hour after work, you want to come? Give me your # I'll text you the details" and then round up your friends and MAKE them go out after work - it'd be too weird if all of a sudden you were like, "oh, people cancelled, do you still want to go?"
posted by KateHasQuestions at 2:38 PM on June 3, 2009 [1 favorite]
Interns are usually young, usually smile in order to make a good impression, and often have no idea about power dynamics, their own attractiveness, how innocuous body language may misinterpreted, that sort of thing.
Why not ask her out for lunch, but it sure seems like you're misreading the situation.
posted by KokuRyu at 3:08 PM on June 3, 2009 [2 favorites]
Why not ask her out for lunch, but it sure seems like you're misreading the situation.
posted by KokuRyu at 3:08 PM on June 3, 2009 [2 favorites]
What Cricket said -- why not just wait till the day after the damn internship ends?
posted by paultopia at 5:02 PM on June 3, 2009
posted by paultopia at 5:02 PM on June 3, 2009
When you're over 35, with a couple of kids, a mortgage, a minivan and guinea pigs, you learn very quickly to differentiate between a come-hither smile and a smile that is basically the equivalent of a puppy-dog wagging its tail and licking the hand of one and all.
posted by KokuRyu at 5:29 PM on June 3, 2009 [1 favorite]
posted by KokuRyu at 5:29 PM on June 3, 2009 [1 favorite]
You like her, and unless you can stop liking her, it can get get awkward no matter what. I'm not sure why you're asking all of us for advice. You need a man on the ground. Talk to a co-worker, preferably female that you trust to gauge the situation. Ask her if you would come off as creepy asking the intern out to lunch.
Don't give up just based on KokuRyu's advice; it's good advice and all, but I know of people that have entered into good relationships in (or rather, in spite of) similar work dynamics.
posted by jabberjaw at 6:56 PM on June 3, 2009
Don't give up just based on KokuRyu's advice; it's good advice and all, but I know of people that have entered into good relationships in (or rather, in spite of) similar work dynamics.
posted by jabberjaw at 6:56 PM on June 3, 2009
I like disillusioned's idea. Except that email sounds a bit off. In-person, direct approach is better IMHO.
posted by xm at 7:27 PM on June 3, 2009
posted by xm at 7:27 PM on June 3, 2009
I don't know if this will end up coming in too late, but if she actually suggested you stop by her desk sometime, and she made it clear where she worked, it sounds like an invitation to me (although not necessarily for a subsequent lunch, etc). If she really wanted no part of you, she easily could've just been polite like she would have to anyone else, and ended it there.
The simple thing to do might be to stop by her desk, ask how she's doing, let her know what your day is like, see if you have any common background details, and so on. Being the new person at work can be intimidating, and having you as a sort of ally can make her feel at ease around you. If the worst that comes out of this is a platonic friendship, that's not bad.
Maybe let her know where you work, and offer her to visit you (if feasible) and see what your work area is like. It should be pretty easy from there on out. Yeah, you could wait until her internship ends, but I'm sure she'd appreciate you giving her someone to confide in at work in the meantime. Good luck.
posted by TheSecretDecoderRing at 11:40 PM on June 4, 2009
The simple thing to do might be to stop by her desk, ask how she's doing, let her know what your day is like, see if you have any common background details, and so on. Being the new person at work can be intimidating, and having you as a sort of ally can make her feel at ease around you. If the worst that comes out of this is a platonic friendship, that's not bad.
Maybe let her know where you work, and offer her to visit you (if feasible) and see what your work area is like. It should be pretty easy from there on out. Yeah, you could wait until her internship ends, but I'm sure she'd appreciate you giving her someone to confide in at work in the meantime. Good luck.
posted by TheSecretDecoderRing at 11:40 PM on June 4, 2009
This thread is closed to new comments.
posted by Bakuun at 11:08 AM on June 3, 2009