How do I start a conversation with someone?
March 26, 2008 4:46 PM   Subscribe

There is a boy. I work at the same place as him, but in a completely different department. Face time is minimal -- what is the least freakish way to start a conversation?

I barely see him around the office. Just occasionally. But I do know his name. Would it be weird to e-mail him? Should I just stake out the bathroom and hope to run into him?

PS: I am terrible at starting conversations and I am scared crapless. Tips on good, flirty first impressions would be appreciated. Thank you.
posted by als129 to Human Relations (30 answers total) 10 users marked this as a favorite
Man, I don't know about you guys over in Dept X, but in Dept Y policy F drives me nuts!
posted by phrontist at 4:56 PM on March 26, 2008 [1 favorite]

Do all office workers eat lunch at the same time/location or does he have a 'regular' place to eat? Try looking into that or perhaps seeking out a mutual acquaintance. Emailing him wouldn't be strange at all as long as he knows who you are; just try to find a hook with any approach you take.
posted by cgomez at 5:08 PM on March 26, 2008

If you want to MeMail me, I will help you brainstorm, but I need more specifics - size of company, any mutual work acquaintances, do you know when he goes to lunch (can you run into him on the way out of the building? any mutual people that might be eating with him, going to happy hour, etc?), ages of parties involved, what kind of company (for subject matter purposes).

All of that said, don't stress it, if you can help it, and don't go overboard trying to run into him. When you see him in the halls, a friendly smile and a "hey, how's it going :)" - being awkward at stuff like this is often in our own heads, and we are often our own toughest critics.
posted by KAS at 5:13 PM on March 26, 2008

Ugh, sorry, that sounded all creepy of me, like "tell me every single thing about your work life" - I was just thinking of the things I would ask a friend, or a friend would ask me, if we encountered the same question for ourselves.
posted by KAS at 5:15 PM on March 26, 2008

I dated a woman I met at work for while. We'd met, and weren't likely to meet more than once a month. She'd introduced herself and been friendly, but at the time I wasn't interested.

Anyway, I emailed her months later and we started having lunch.

So maybe, "hey this might sound weird but do you want to have lunch sometime?"

If someone said that to me, I'd probably have lunch with that person.
posted by sully75 at 5:16 PM on March 26, 2008 [1 favorite]

Btw, if you said exactly this: "Man, I don't know about you guys over in Dept X, but in Dept Y policy F drives me nuts!" I might fall in love with you right away. YMMV.

Another way of saying that is, tell a joke! Make it good. Also, smile and look him in the eyes every chance you get. Do you ever walk by his desk/office/cube? Introduce yourself in a friendly way and leave it at that. The trick is to build up a sense of familiarity so that each interaction builds on the last. Start asking about him, what he does, where he lives, how his weekend was.
posted by wemayfreeze at 5:25 PM on March 26, 2008 [4 favorites]

If you want to start by emailing and have already had a conversation with him, just email him a followup to the conversation. Something like, "Oh, and I thought of another thing about [whatever we were talking about]..."
posted by ignignokt at 5:25 PM on March 26, 2008

You have to have a hook -- something to talk about once you get the first hello out. If you're sure he knows who you are, and you see him wearing something particularly notable one day it probably wouldn't be too weird to email him about that. You know, a "hey, I saw you had on a Penny Arcade shirt! Teh awesomez! Have you ever been to PAX?" Or, you know, whatever. The key is to find something that will be an icebreaker and give you an excuse to compliment or ask about it. But also something that will give you a follow-up question, so he doesn't just tell you where he got the shirt, shoes, cubicle toy, etc.

If the initial contact goes well, now you have an excuse to talk to him when you see him around the building. Pretty soon you're that girl he talks with about foo. Then you invite him to wait for it... bar.

Basically, what you're trying to do is get to know the guy and let him get to know you so that there's something between you other than "OMG, he is teh hott."

I met my current boyfriend (well, was reintroduced to him after a few years) when he was out with some friends of his at a bar, and I was at the end of a two year long relationship. I thought he was pretty adorable, and wanted to find out more. Fortunately, I found out that night that he had just moved into a house a few doors down from me. We chatted a bit that night, and then I added him as a friend on Facebook. (Yes, I know, supposedly we're all too old for that.) That gave me a chance to learn a little bit more about him, and vice versa. A month or two went by and after I was out of my previous relationship started chatting with him online. Eventually this lead to a discussion of our mutual fondness for whisky, which gave me the perfect opening to invite him over one night "if he ever needed to borrow a cup". He came over a couple of times, each leading to several hours of talking as we got to know each other better. Finally, a month or so later I laid it on the line and asked him out. Luckily, he said yes and we're still dating today.

But the most important part was finding a way to get to know him, so that I could see if he was even someone I would want to date before I got too worked up over whether he liked me too. So start small, and good luck!
posted by MsMolly at 5:30 PM on March 26, 2008

Don't you guys need some help from the accounting department anyway? I also heard they have extra post-it notes on that floor, which will help since you just ran out.
posted by salvia at 5:33 PM on March 26, 2008

seller's market. seriously.

grab him by the nearest analog to a collar and say whatever comes to mind.

or whisper.

or just release him from your grasp and walk away.
posted by stubby phillips at 5:42 PM on March 26, 2008

Response by poster: stubby: seller's market? I'm not following.

Grab him? Whisper? I can't do that stuff! I mean I could, but he'd probably call security.
posted by als129 at 5:46 PM on March 26, 2008

So maybe, "hey this might sound weird but do you want to have lunch sometime?"
If someone said that to me, I'd probably have lunch with that person.
posted by rokusan at 5:50 PM on March 26, 2008

Just tell him you noticed how hot he was. That will probably work.
posted by delmoi at 5:51 PM on March 26, 2008

get right in his way.
look him in the eye.
say hello.
posted by stubby phillips at 5:54 PM on March 26, 2008 [1 favorite]

Tell him you have "this friend" who wants to ask him out for lunch. Ask him how "your friend" should go about doing that. C'mon, it'll be funny. He'll know you mean you, and either tell you yes or some excuse why not (which means no).
posted by ctmf at 6:02 PM on March 26, 2008 [1 favorite]

first time you run into him: make eye contact and smile.
next time: make eye contact, smile, and say hi.
third time: make eye contact, smile, and say, "we meet again."
fourth time: make eye contact, smile, introduce yourself.
etc etc etc.
posted by thinkingwoman at 6:03 PM on March 26, 2008 [1 favorite]

"Whose that cutie in Accounts Receivable?" to a friend in that department will work just fine.

Unless he's Herbert Kornfeld.
posted by Ironmouth at 6:17 PM on March 26, 2008 [1 favorite]

Best answer: als129, "seller's market" meaning that you're the seller and odds are in your favor.

"Hey, I'm kinda hungry, you feel like grabbing a bite with me?" And if he's brought his lunch, then set a date for next week. That, or just grab his tie in the hallway and push him into the office pantry.
posted by hobbes at 7:07 PM on March 26, 2008 [1 favorite]

The next time you see him in passing simply smile and say "Hi"- you don't need to say anything else.

He will get the message.

The next time you cross paths he will say "Hi", and if you pause he will probably initiate a conversation. If he doesn't no big deal- he might be scared too, like 99.9% of the rest of us.

After a few Hi's you will have something in common and it will be easier to strike up a

And that's how I got arrested for stalking (I kid)
posted by mattoxic at 7:08 PM on March 26, 2008

My boyfriend and I worked together when we first started dating. He got me to keep coming over to his office by keeping an ever-changing supply of candy and baked goods in one of his desk drawers. You should try that.
posted by amarynth at 8:43 PM on March 26, 2008

Lots of high school advice. Which is cool if you're looking for that sort of thing. I prefer being approached directly.

Best introduction I've ever received:

"Hi. My name is yOinnigH. You're name is GPF, right? I don't mean to be too forward, but would you like to have dinner sometime?"

ad lib small talk as necessary

"I don't mean to be too forward" = yes, I'm interested in you
"dinner" != casual lunch because I'm bored at work

No tactics or subtextual strategy needed.
posted by GPF at 8:53 PM on March 26, 2008

Note: I'm speaking from the perspective of a 20-something male who's just started dating again.

I'm assuming you're a girl. If you are reasonably attractive, and he is single (and often if he is not, but let's not go there) then it is 95% certain he'd be willing to take you out on a date.

What you need to do is, the next time you see him, stop what you are doing, walk directly over to him (holding eye contact if he sees you) and just say "Hi! I'm als129. You're really cute. You should ask me out."

Substitute 'cute' with the compliment of your choice, and try not to laugh at him as he stammers out a response.
posted by Ryvar at 10:39 PM on March 26, 2008

Don't do the ryvar thing. It's too aggressive. Just smile and say hi. Next time, say - so, what's your name?
posted by markovich at 1:39 AM on March 27, 2008

Tell him the shirt he's wearing is a nice color on him. Ask him if he's ever had the tuna salad from the kiosk, and does he hate the tarragon in it, too? Ask if he saw Lost last night, or the Knicks game, or Masterpiece Theatre. Don't overthink the plate of beans. The key thing is to initiate any conversation. You're feeling way awkward; it's okay. He'll appreciate being chatted up. He's likely trying to figure out how to initiate conversation with you and will be delighted. And if you keep telling yourself that, then you will feel less awkward.
posted by theora55 at 8:04 AM on March 27, 2008

Best answer: Jesus christ.

Walk up to him when obviously not too busy or doing something that looks important.

This is the tricky bit. Say these EXACT words.


Smile, not weirdly.

Let us know how you get on.

Seriously, how do you people ever get to procreate?
posted by daveyt at 8:21 AM on March 27, 2008

Yeah, let us know! I wish there was a Follow-Up section around here somewhere. I locked my keys in my Dodge Intrepid last night wondering whether she found panty hose that fits, and what talent this one's been working on to impress her abroad boyfriend. I get so caught up in these predicaments, I feel like this one.
posted by thebellafonte at 9:27 AM on March 27, 2008

als129, at the risk of sounding overly-solipsistic, I think it's pretty obvious that you must be that girl I just saw in the cafeteria a few minutes ago. Given that that's the case, I would be delighted to receive an e-mail from you.

You could even make it something tangentially related to the department I work for to be all smooth about it, like "Hey, I need to contact Person X in Accounts Payable, and I think your department works with him; what's his e-mail address?" and then throwing in something personal to the e-mail, too, like "Sorry I can't seem to find his name in the company directory, I'm feeling a little spacey today because I was up late last night."

Which would then afford me the opportunity to not only say "Hey, here's the contact info for the guy you're looking for," (I get a sudden boost of joy from knowing I helped you), but also "Why, what were you up to last night?" (I further a non-work related conversation).

And then that's a whole non-work-related e-mail conversation that springs up during the workday, and then you can, at the end of the workday, end the exchange with, "Oh, by the way, I was thinking about checking out New Place Y this evening, you wanna come?" And then I'd be all, "Yes, that sounds GREAT!" or, if I'm busy, "No, I can't, but I'd be happy to go to Place Y or Some Other Place tomorrow / this weekend / next week."

als129, I believe this course will work out quite well.
posted by Greg Nog at 9:51 AM on March 27, 2008

Response by poster: I will update this post after it goes down. Hopefully by tomorrow?

I feel nauseous.
posted by als129 at 11:07 AM on March 27, 2008 [1 favorite]

Good luck - you'll be fine.
posted by Nick Verstayne at 11:19 AM on March 27, 2008

Do you need to be in such a hurry to start an actual conversation, per se?

If you think of it as just initiating contact, you can take some pressure off yourself - a brief smile when you pass, for example. Plant a germ of a thought in his lizard brain. After a while, he'll come to recognise you as that nice & friendly girl who always smiles "hello" when she sees him.

Just remember: a journey of a thousand miles starts with a single step. The actual step itself isn't so important; just the fact that you've taken it.

And 90% of communication is non-verbal, anyway.
posted by UbuRoivas at 5:24 PM on March 27, 2008

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