How do I let a coworker know I'm unequivocally interested in him?
September 19, 2013 6:12 AM   Subscribe

With the caveat that I know 'shitting where I eat' is a bad idea, I'd like to let a coworker know I'm interested in him. Asking him out isn't an option too, because I'm pretty shy and would probably blush and flub anything that's supposed to be casual. How do I do this? We have zero interaction.

Here's some background:

1. We work on the same (big) floor, in completely unrelated departments. However, we seem to run into each other walking in and out of conference rooms, hallways, even the restrooms (men's/ women's are next to each other). We even park in the same row of the parking lot (found that out by chance a few weeks ago).

2. I know his name and where he sits, but I don't know if he knows who I am. What I do know is that he's noticed me, because he'll say hi, but no eye contact and it's fleeting. Out of the corner of my eye, I've seen his gaze follow me. There's been a couple times when I've tried to make eye contact, but he's already looking away. I can't imagine he's shy because he's a senior marketing manager (and has a TON of work-related social interaction).

3. Speaking of seniority, I'm fairly high up in my own right, and there's no danger of him ever being a supervisor (completely different, unrelated departments with different org structure).

4. I'm in my early 30's - no idea how old he is. Probably between 33-38.

5. If everything I've noticed about him sounds creepy or obsessive, it isn't. I'm an extremely observant person and always aware of my surroundings no matter where I am.

6. We've had a work happy hour (these are huge shindigs with over a hundred people at least - the company is big). We've seen each other at these things but we're both in groups of people (no overlap), so it's been hard to say anything - at least on my end.

7. I have no idea if he's single, but he wears no ring. Heck, I don't know if he's straight, but it's hard to think he isn't. My (usually good) gaydar isn't going off.

I'd like to let him know I'm interested. We're both extremely busy, lots of responsibility, but I think young enough that enjoying flirting isn't completely out of the question ;) Not to toot my own horn, but I'm very attractive and get a lot of attention from male coworkers (no, I don't dress provocatively, jeans and sneakers usually), and I have an advanced degree. Women like me - I'm friendly and warm, but quiet. Possibly quiet to the point of being misunderstood as snooty, but most people say the minute they speak to me that notion eva

It pains me that this crush is occupying so much of my mental energy, but he's smart and well put-together (I've heard him speak, and most women wouldn't think he's conventionally attractive). Any ideas on how I might convey my interest/ give him the opportunity to ask me out? Start up a conversation? I've thought about throwing caution to the wind and introducing myself, but then what?! I'm too shy and awkward to make small talk and there's really no opportunity to do that (when he's walking out the bathroom? when we're both rushing to meetings?). Complimenting him? On... his business casual 'uniforms'? I don't walk by his cube ever.

God, this is so silly.

Ok, I'll stop acting like an overthinking high-schooler and try to be a little more mature about this. Should I just forget this whole thing? I'd really rather not, MeFites. Thank you so much :)

P.S: I'm great at being NOT awkward (I've never let dating situations get weird - never dated at work before, but have been asked out.... and even dating situations outside of work involving friends or acquaintances). And no, I don't know anyone that knows him.
posted by anonymous to Human Relations (30 answers total) 2 users marked this as a favorite
 
You have two choices:

1. cross his path frequently and hope he asks you out.
2. ask him out. On a "date". Don't ask him to help you clean out the grease trap and hope he will infer datelike qualities from that.

Either ask or wait to be asked, there's no in between. You have a brief window just for creating a preparatory Air of Mystery, but it is briefer at work than in any other social context. In the workplace, prolonged ambiguous lurking and slurking is creepy.

You don't know if he's married or attached or even straight? It is as if social media had never been invented. Look him up.
posted by tel3path at 6:20 AM on September 19, 2013 [12 favorites]


You can ask him out for coffee, it's pretty easy, "Hey, I see you around the halls all the time, I'd love to know more about what you do around here, want to grab a coffee some time?"

See what he says, if he seems open, suggest going to the Starbucks in your building (or whatever) at around 10. That way it's going to be short, but away from work. You can suss out the situation. If he's single, and interested you can offer, "Gee, you're fascinating, I'd love to take you for a drink after work."

You are a grown woman, if you can't say these things to a co-worker, I dispair of you.
posted by Ruthless Bunny at 6:20 AM on September 19, 2013 [19 favorites]


there's no danger of him ever being a supervisor (completely different, unrelated departments with different org structure

I'm not sure if this matters - management is management, and if he's higher up in on the org chart than you are, it might still skirt the line for him.
posted by jquinby at 6:21 AM on September 19, 2013 [1 favorite]


I think this is a bad idea. It's a crush, and it's a crush from afar. It's not even, we get along great and have tons in common, it's I noticed he parks in the same row as I do in the parking lot. All of your background could apply to half the people you work with. Saying hi in the halls and watching you walk away are not evidence of interest.

That said, if you want to ask someone out, ask him out. But make sure he knows it's a date with romantic interest. Don't pretend it's happy hour or work-related or anything else. Let him make an informed decision to spend time with you.
posted by headnsouth at 6:24 AM on September 19, 2013 [6 favorites]


He looks at you sometimes. He parks near you sometimes. You've heard him speak before.

Is it possible that you might not actually know shit about this guy at all?
posted by oceanjesse at 6:25 AM on September 19, 2013 [7 favorites]


You could leave a note on his car.
posted by JohnnyGunn at 6:29 AM on September 19, 2013 [1 favorite]


In my opinion, your crush isn't creepy yet - it's sweet and pretty goofy - but since you really haven't gotten any unequivocal positive feedback from him yet, and you don't actually know a single thing about his personality, I would a.) keep it very, very casual (no direct asking-out yet) and b.) try to accomplish whatever you're going to do quickly so you don't spend too much time stewing.

This is what my plan would be in a similar situation:

1.) Next time you see him around, escalate the conversation beyond "Hi." Just to a few pretty bland words, but delivered with a big smile. "You again?, "Nice tie," "Nice car," "So...how 'bout them Yankees," etc. It's not easy but it's not rocket science. You can figure something out. Do this tomorrow.

2.) When's the next big shindig? I hope it's this weekend. If it's at least this month, do your best to talk to him, or to at least be in the circle of people he's in. Without paying him an inordinate degree of attention, try to find out the few major facts about him (gay, straight, married, etc.) and make sure he learns your name. If you absolutely can't do that, do some very, very low-level lurking - like at least try to be in the same space with him and exchange a few glances. Don't play this off as 'Oh god I'm dying of love for you,' just that you're obviously trying to say hi and you can't get the opportunity, and it's maybe amusingly frustrating.

3.) Post shindig, if you haven't spoken yet, go up to him at his desk - if it's that kind of office - or, if not, the next time you see him, and say, "Hi, my name's X and I feel like I see you around everywhere. What's your name?" Ask this even if you know his name unless it would be blatantly obvious that you're faking. If you already talked to him at the party, say, "Hey, X, blah blah joke about something you talked about blah blah blah."

4.) If generally, in all of these interactions, he seems eager to talk, smile back, gives good body language, etc., after you've had one long workplace conversation, friend him on Facebook (if he's into that sort of thing). If not, send him one friendly, funny work related email. Just a line or two.

5.) After this level of friendship has been established, if he has, at least once, reached out to you - to say hello, talk, and so on - invite along him on one group outing. Throw a party, if you're a party thrower, or go out for birthday drinks, or something.

If he comes along, you're entering into regular flirting territory. If he says no without offering an alternative plan, drop it forever.

That's probably too much time and energy invested in something that's likely to turn out to be nothing - my guess is you'll lose interest after step 2 - but if it's fun and helpful to have a plan, there's your plan.

Update me if it works. Good luck!
posted by pretentious illiterate at 6:36 AM on September 19, 2013 [12 favorites]


Step one is have a conversation with the man as a person instead of as a love interest. This is advice that men get all the time - he is a person. Think back to the times when men wanted only to get into your pants. How uncomfortable was that? Now think back to the times people had genuine curiosity about you and your work? Start there. This may be something as contrived as shooting him an email about something his department and your department can collaborate on. Or you could stop by his group at the next happy hour and say hi to someone in his group that you know, and then turn to him and mention that you've seen him around, ask how he's liking the company so far (if he's a recent hire) or what his current big project is. Better still, find out what his current big project is. Maybe your big organization has channels for this kind of information to flow through. Be careful with these though, because (some) people will gossip. Do not let your intentions ooze out while you gather data. That will seem creepy.

The reason that is step one is because you need to take a step back from your crush and learn something about this guy. Maybe he smashes kittens against rocks for fun, or is married, or prefers dudes, or drinks to excess every night. Evaluate the facts you gather in as objective manner as possible. None of that "well, he only smashes one kitten a year" thing that is so easy to do. Once you have actual information about who he really is, then decide if you are interested, and then, MAKE IT CLEAR by asking him on a date.

There are at least two steps between parking near someone and alerting them that you are interested.

Neither flag code nor some secret handshake will help you get from point A (see him around) to point B (on a date with him). There is no dance you can do in front of the bathroom as he exits that will alert him that you'd like a relationship with him, or even to get to know what his politics/life goals/etc are.
posted by bilabial at 6:39 AM on September 19, 2013 [11 favorites]


You are a grown woman, if you can't say these things to a co-worker, I dispair of you.

Oof, I wouldn't be able to either! I met Mr. Llama at work and I only wound up married and having a kid with him because I got him drunk at an office Christmas party.

Can you manipulate some kind of cross-department exposure, and float things in your department about getting some feedback from marketing or something? Just so it's incrementally less weird to say 'hey, you want to grab coffee?'

Other than that, wait for another one of those work happy hours and make it your mission in life to a) come up with something to say to him when you have the opportunity and b) watch him for the opportunity, for when he drifts away from his group to go get another drink or whatever and then make like a talky person.

If you do this once or twice, it will start being less weird, and then you might be able to transition into something a little more direct.

(I too am wimpy about direct approaches.)
posted by A Terrible Llama at 6:42 AM on September 19, 2013 [4 favorites]


You want to let him know you're interested, but not ask him out? That's completely backwards. You know NOTHING about this guy- you absolutely need to ask him out for coffee or something, as laid out in previous answers, so you can figure out if the crush has any chance of going anywhere. Drop the CRUSH bomb on his lap now and you could very likely explode the whole thing; what do you expect him to do with that random, weird information? Start small. Coffee. Danish. Something.
posted by ThePinkSuperhero at 6:43 AM on September 19, 2013 [2 favorites]


For the record, I knew my boyfriend all of 5 minutes before I asked him out. We were physically attracted to each other and that was enough for us to want to get to know each other.

YMMV but I failed every time I tried to hem and haw and flirt to see if a guy was interested. A very direct approach is the only thing that's worked for me in my dating life.
posted by girlmightlive at 6:46 AM on September 19, 2013


It doesn't seem like you've ever had a single conversation with him about anything, am I reading this correctly? Further, you say you are super awkward and uncomfortable with small talk. I'm wondering how you envision a date will go in this situation? Do you expect him to carry on the entire conversation?
posted by elizardbits at 6:47 AM on September 19, 2013 [13 favorites]


You don't know anything about this guy. You need to know something about this guy before you ask him out, so that a) you don't seem like a creeper, b) you don't put him or you or both of you in a bad situation, and c) you actually have something to talk about were he to say yes, other than making it an interview-date.

Were I you, I would ask someone in his department about whatever project they might have going on, learn the basics of it. That's work-related, so it's fine. You have now created an in with this guy, to talk to him about that project, which of course, is fascinating and you'd love to learn more about. And you're still within the confines of work.

At that point, he at least knows who you are, that you're friendly, and it's much easier to say yes than were he being asked out by a total stranger (which you are right now). And who knows what you learn about his situation during your initial recons, anyway?

Without the foundation of him at least knowing something about you first, your chances of success are pretty slim.
posted by Capt. Renault at 7:03 AM on September 19, 2013


I am very socially awkward. I am a woman. Nerdy in the nerdy sense, not in the "oh, yes, I'm such a Nerd!" sense. I would not have the social skills to pull off this kind of intra-workplace interaction. You should consider whether you do, indeed, have it together enough to date someone at the office.

But you like him. I get it. You can make yourself crazy wondering. I've done that many times before. Past a certain age I got sick of that and then started asking people for coffee. Including, a few ill-advised times, at work. Sometimes it led to coffee! If it never went beyond that, it's because I've been in a relationship for the majority of this era of my life...only had a few months to "experiment" here and there.

You know what you have to do. So you can either do it or make yourself nuts until you move on in your mind. Go for it! Men have an advantage here--traditional gender roles tell them it's their JOB to step up. So now it's your job.
posted by skbw at 7:17 AM on September 19, 2013 [1 favorite]


Not to toot my own horn, but I'm very attractive and get a lot of attention from male coworkers (no, I don't dress provocatively, jeans and sneakers usually), and I have an advanced degree

Then what seems to be the problem? I mean, you're a catch, right?

If you are determined to convey your interest, you need to be direct and ask him out. Indirect romantic-comedy behavior will not work. I have never dated anyone in the workplace (which I think was a sound practice), but I think the best time for you to express your interest is not "on the clock". For example, if there is another office happy hour coming up, or perhaps if you run into each other in the parking lot after work. But, really run into him. People tend to have a good sense of when someone else is doing something accidentally on purpose.

He's likely not going to be very interested in your degree.
posted by Tanizaki at 7:17 AM on September 19, 2013 [6 favorites]


You don't know him at all, so that's the first order of business. I find it's easy enough to hold out my hand to someone I've seen a number of times in my building and say, "Hey, we haven't officially met yet...I'm Patrick." I then ask a few questions about what they do, where they commute in from, etc.

If you find the guy interesting enough after that short conversation, ask him to coffee or lunch to get to know one another and what you both do in the company. That allows both of you to get to know one another in a professional way, and if it doesn't work out in any other way, you've avoided the weirdness of moving too quickly AND you've made a new ally at work...win-win!
posted by xingcat at 7:18 AM on September 19, 2013 [5 favorites]


Figure out an excuse to talk to him. It can be a completely flimsy, dumb excuse, but you need to go talk to the guy. "Giving him the opportunity to ask you out" is not a thing that's going to work. He has the opportunity to ask you out right now. Nothing is going to get you what you want but you talking to him.

I don't walk by his cube ever.

Here is something that may help you in other situations besides this one: People outside of your immediate area of interaction do not notice you. They don't pay attention to your habits (unless, as demonstrated in your post, they have a crush on you). In those moments when you do enter their sphere of awareness, they are not overthinking it the way you are. What I'm saying is that if you do wind up walking by his cube, I guarantee you that he will not be thinking, "Hey, wait a minute! Anonymous never happens to walk by my desk! I detect skullduggery!" No, if he takes any note of you at all (he won't), he will just assume you have a reason to be doing what you're doing. But it won't even be that conscious of a process for him.

So walk by his cube. You don't need a reason. Go to the bathrooms on the other side of the office and play some Angry Birds or whatever and then, on your way back to your desk, talk to him about whatever your excuse to talk to him is. A prominent photo displayed in his office. Whatever.

Pay attention to how conversation flows. If something happens, great.

If something doesn't happen, then talk to him at the next happy hour. You now have an in, so use it. Keep paying attention to the way conversation flows. If he's just kind of perfunctory about it all, abandon ship. If you can't have a naturally flowing conversation with him then you shouldn't be trying to date him.

Do all of this as soon as possible. Create a conversational inroad with him before the next happy hour, and capitalize on it then. If this goes on too much longer, you're going to keep building it up in your head and it's not likely to go great.
posted by FAMOUS MONSTER at 7:54 AM on September 19, 2013 [3 favorites]


Not to toot my own horn, but I'm very attractive and get a lot of attention from male coworkers...

Including him?

If not, then this may be partly fueling your mega-crush. Since you're already playing the cinema'esque freshman year role, why not just take it a further step in that direction and ask a male coworker who works nearby his office and get the lowdown?
posted by Kruger5 at 8:08 AM on September 19, 2013 [2 favorites]


I think your two best opportunities to speak to him are the parking lot and the happy hours. Come up with a few openers that you could use in either situation.

Parking lot:
1. Hey! How's it going? Boy, Mondays, eh? [You walk into the building together]
2. [Leaving work at the same time] I'm glad it's nice and sunny today. I'm going to sit out on my porch with a book after work and enjoy it!

Happy hour:
1. Find someone you know in his group and go talk to them.
2. Go up to the bar to get a drink at the same time he does.

Basically, you've got to break that casual conversation barrier. At this stage you can use any of the techniques you'd use to meet someone in a work-related context. The goal is not letting him know you like him right away, the goal is to go from "person he vaguely recognizes from around the office" to "Anonymous, who has a cat and works in Systems" (or whatever). Then, when it's no longer weird to have a short conversation with him, use the happy hour after that to ask him if he wants to grab a cup of coffee.
posted by MsMolly at 8:39 AM on September 19, 2013 [1 favorite]


Your question kind of reads as "I'm attractive and smart and interesting, why can't he see that?" And the reason is because he doesn't know you. (Or he's not physically attracted to you, or he doesn't date coworkers, or he's shy, or whatever). To be blunt, he's actually not "noticed you" yet.

The only way that you can let him know that you are interested in him is to actually act like you are interested in him, and the only way that you can do that is by being in his physical space (and actually talking to him will help, but at least being around him will give him a chance to actually notice you).
posted by sm1tten at 8:57 AM on September 19, 2013 [3 favorites]


Chat him up about work and seque into getting coffee to talk more. Mr. Thatone is a former coworker and we've been happily together almost 20 years. It can work!
posted by thatone at 9:06 AM on September 19, 2013 [1 favorite]


I suspect there's a spark - you feel it, and I'll bet he does, too. You've reached the limit of seeing him in the hall, and it's going to take more to make anything happen.

- You know his name and work info. Do you know anybody who knows him? You need to ask somebody if he's single, and ideally, someone who will tell him you asked.

- Has he won any awards, does he have a specialty, hobby, etc? Can you ask to meet with him to get his advice on something?

- Get to work early, listen to the radio until he arrives, then go into work together.

- Compliment him. Nice shoes or Great shirt or Did you get a haircut?

- Fake it. You're Ben in Accounting right? We email all the time?

- Dating_Fails_Fixed has some ideas. and google dating advice, how to talk to guys, etc., lots of cheesy nonsense, but something will appeal to you.
posted by theora55 at 9:18 AM on September 19, 2013 [1 favorite]


Would simply emailing him "FYI - link to your okcupid profile" be an option?
posted by Sophont at 9:29 AM on September 19, 2013


It seems like what you want to do is figure out a way to shift all the risk of this encounter from you to him. The way to do that is to do exactly what you're doing -- you do nothing, and either he does something or he doesn't, but you've done nothing to let on that you're interested, and you've taken no risk. So far, if he's interested in you, he's taking the same approach you are. He's doing nothing, and he's hoping you do something. The result so far is that you've never talked to each other. (And, it must be said, you really don't know whether you'd want to go out with him or not; you like the look of him and the way he engages in public speaking, it sounds like. That's not a lot to go on.)

The other way to go besides the way you're going right now is to take on a small amount of the risk yourself. This requires you to go up to him and say, "Hey, we've never officially met. I'm [Anon], I work in [my department]. I think we park near each other." If he says, "Oh," and he goes back to his work, you will know he's not interested and you can drop it, but yes, you will have to live with the horror of having introduced yourself to a guy who didn't take an interest. But if he says, "Oh, right. I'm Dave, I work [in this job]. You drive the [gray Honda; blue Lexus; green Fiat; black motorcycle], right?" then you are having a conversation. If you don't think you can have a conversation, you are selling yourself short if, in fact, you are warm and well-liked, as seems to be the case.

Here's what I'm saying -- either go say hello or do not say hello. If you are into zero-risk alternatives, the one you're already doing is it, and you probably won't meet him unless something changes. Otherwise, you have to do something, and anything you do that creates visible evidence that you wish to speak to him potentially could be embarrassing, at least a tiny bit. But you will not die from being a tiny bit embarrassed. People do this all the time. They ask other people out, they start conversations, they don't wind up together, they get dumped, and they don't die. This is a good thing to get used to, is my personal opinion.
posted by Linda_Holmes at 11:43 AM on September 19, 2013 [1 favorite]


I just wanted to say Ignore the naysayers. I know a great number of marriages that started at work.

Admiration from afar is fine - he might be holding back for the same reason! You can drop the hints, just be smart about it and PACE YOURSELF. No OK cupid profile links, no notes on the car. Work the social network. Find out if he's single by putting feelers out with people you trust "gee so-and-so seems nice, I wonder if he's married" and see what they say. Chat near his group at the next social function, and VERY casually let it be known that you're single. Then let things brew. If they will grow over time, then it will be undeniable, and if it will fizzle then you'll have a smooth social exit.
posted by St. Peepsburg at 12:19 PM on September 19, 2013


As a fellow sort-of-shy person who only goes to the happy hour if someone on my team is going (I won't go if I don't know anybody), I have some different advice.

Lately, I've started to absorb the seemingly common knowledge that work is halfway about Networking. I've written it down on my annual goals, and I've let my supervisor know that I am going to try to go outside my comfort zone and introduce myself to people outside my team.

And I've done it. Went to a training class last week and just walked up to people saying "I've decided to try to meet people in this class; my name is CathyG and I work in X Dept" and I stick out my hand for a handshake. I met 6 people over those 3 days - one of them turned out to have gone to my obscure elementary school 1000 miles away, another turns out to write the same kind of reports for his team that I write for mine (future collaboration) etc. It has REALLY improved my worklife, even just in a few months.

Oh, I did the same thing in my water aerobics class, which I've gone to for 3 months knowing nobody and I assumed they all knew each other. Guess what? NOBODY knew each other, so I started a "meeting folks" revolution. And you know what else? Everyone was happy I did it, and not one person responded to my greeting with "fuck you".

You could do this. You probably have annual goals that you have to submit, and you hate coming up with "be more organized" or "follow up more". Well, here's a goal: Be better at networking in the office. Then pick out several people and just introduce yourself. xingcat as it above: hold out my hand to someone I've seen a number of times in my building and say, "Hey, we haven't officially met yet...I'm Patrick." I then ask a few questions about what they do, where they commute in from, etc.

Once you've done this and your coworkers know you are doing it, THEN you can approach your guy and just do the same thing. Once you've met him, you can figure out how/if to take it further.
posted by CathyG at 1:01 PM on September 19, 2013 [4 favorites]


You're in your early thirties and definitely over-thinking this. Walk up to him next time you see him and invite him out after work for dessert and coffee (not drinks, never start with drinks).

Over coffee tell him you saw him and he intrigued you. If he is available, that is. If he's not available and declines then you know it's not to be. This isn't rocket science, just human nature! Good luck!
posted by pink candy floss at 1:16 PM on September 19, 2013


It's interesting that you say you're shy but what you want to do - "let a coworker know I'm unequivocally interested in him" - takes far more courage than what I think is the obvious way to go, and what a number of people have suggested: just introduce yourself and see if you guys start to talk occasionally. I mean, there are ways you could let him know without technically asking him out, like saying "We keep bumping into each other! You need to just ask me out already!" But that's almost as bold as just asking him out yourself. (Though saying it after you've had a number of conversations about your shared love of outdoor concerts or whatever is not.)

The other thing you could do, though I'm not sure if I'd recommend it because there are many ways it could go wrong, is if you have a female friend at work who is extremely outgoing and sort of the nosy type, she could start talking to him and put ideas in his head about you and eventually introduce you/set you up. Especially if she's older and/or married, so it would look like the standard "Oh no, people are single! We can't have that!" deal. I've seen situations where this kind of thing would have worked if both parties were interested. But all of those involved people in more entry-level jobs with less to lose. So again, I don't know. But it's a thought.
posted by DestinationUnknown at 2:02 PM on September 19, 2013


Hmm, I would like others suggest getting to know literally anything about him first, but before that even, save yourself some trouble and find out if he's single. You could have some chitchat with him, or just find someone in the office who knows. Could save you a bit of trouble.
posted by smoke at 4:22 PM on September 19, 2013 [3 favorites]


I agree with CathyG. You want to approach him as a coworker first, then get to know him as a person, then see if there's any chemistry. Why rush? There's too much at stake and you're in the same place every day. You have a bevy of possibilities, many of which have been mentioned above.

Here's another one. Next time you're standing near each other say: "So I feel like I see you everywhere. My name is Anonymous in DEPARTMENT. You are? Pleasure to meet you. Actually I've been meaning to meet some of the marketing folks. I had a quick question about X. Maybe I can I shoot you an email? Great, thanks!"

Then shoot him your email. Thank him for his reply. Next time you see him thank him again, look into his eyes and smile (you're telling him you like him). Next time let him initiate the chat, maybe say, "Actually I'm taking an office poll. Who do you think has the best lunch?" Next time let him initiate a chat again (this helps you figure out if he's interested) Look him in the eye and smile.

Next time ask him how his weekend was or about his vacation plans. But also let him initiate chats with you. Gradually find out about his interests, his relationship status, what you have in common. Maybe he'll send you a link to something and you'll send him one.

At this point if he hasn't asked you out already, suggest you have lunch sometime. During lunch, or a subsequent lunch, if he seems interested but he's too shy or oblivious to what's going on to initiate something, say something bold like "I'd love for us to continue our conversation over dinner sometime." If after dinner sparks have yet to fly you should either just be direct and say, "I'd love for us to go on a date, maybe see a movie" or move on because in my experience you'd know something by now.

Keep in mind that one classic way a girl lets a guy know she's interested is by saying, "I'd like to go do X." That's the opener for him to say, "Actually I've been wanting to do X, too." And they agree to see it together, they get married and have kids (in the fifties at least).

BTW, there's nothing wrong with just asking a guy out. I just think you need to play it safe in the workplace.
posted by lillian.elmtree at 6:11 PM on September 22, 2013


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