'Best' way to ask out a coworker for a date?

[JEG88]

First off, not trying to actively date a current coworker, per se. I recently got a new job, and will be giving my notice this coming Monday.

I've become interested in a female coworker of mine, and this change in job circumstance has opened the door for me to finally shoot my shot. (I'm a pretty introverted and shy guy with social anxiety, so this would be a fairly significant undertaking for me, as far as putting myself out there.) I worked with her at a previous company, but we've never been particularly close. We typically just say hi in passing at the office, or small talk kind of thing. We did take a walk during a lunch break a few months back to catch up as well. I do think she's intelligent and beautiful, and she seems like a good person.

I'm thinking of asking her to go on a walk again during a work break before I leave, to be able to talk to her and ask her out. I realize it will blindside her and put her on the spot either way given that we don't regularly talk, but any advice on how to transition the conversation to ask her out as seamlessly as possible? I would normally want to build upon more consistent interactions, but given my inherently limited time to ask her out, there aren't many other ways of going about it I feel. At least on a walk, it is away from the office to avoid gossipy eyes/ears.

Assuming we're on the walk, after general small talk and my new job info - I'd go into saying it's been great knowing her, and if she would be interested in going out some time. Trying to keep it simple and not overthink, but would not want to frame it as apologetic about asking out of the blue - would come across lacking confidence if I said it this way I think. Either way, even if she were to say no, I would be proud of myself for even asking at all.

Thoughts? Much appreciated!

[smackie9]

Yes if I was asked that way it does come off lacking confidence. A confident guy doesn't leave the decision up to her, no different than asking if you can kiss her *ugh* I always got turned off by that kind of stuff...you just do it and ask her out. You don't say things like "would you go out with me sometime" lame. You say, hey would you like to go for a drink after work. There's this cool place just down the street.

Edited July 24, 2022 by smackie9

[ExpatInItaly]

Before giving further advice, do you know for sure that she is single, OP?

[Wiseman2]

1 hour ago, JEG88 said:

. I recently got a new job, and will be giving my notice this coming Monday.

I've become interested in a female coworker of mine.

Stay in touch via LinkedIn.(or other social media). That way, After you formally resign and have started at the new place, you will have her contact info and can start a conversation from there. 

Don't make it awkward by prematurely "shooting your shot". If she's interested, she'll be just as interested after you resign.

No need to make yourself anxious or her uncomfortable. Why can't this wait until you are in the new job?

[glows]

3 hours ago, JEG88 said:

First off, not trying to actively date a current coworker, per se. I recently got a new job, and will be giving my notice this coming Monday.

I've become interested in a female coworker of mine, and this change in job circumstance has opened the door for me to finally shoot my shot. (I'm a pretty introverted and shy guy with social anxiety, so this would be a fairly significant undertaking for me, as far as putting myself out there.) I worked with her at a previous company, but we've never been particularly close. We typically just say hi in passing at the office, or small talk kind of thing. We did take a walk during a lunch break a few months back to catch up as well. I do think she's intelligent and beautiful, and she seems like a good person.

I'm thinking of asking her to go on a walk again during a work break before I leave, to be able to talk to her and ask her out. I realize it will blindside her and put her on the spot either way given that we don't regularly talk, but any advice on how to transition the conversation to ask her out as seamlessly as possible? I would normally want to build upon more consistent interactions, but given my inherently limited time to ask her out, there aren't many other ways of going about it I feel. At least on a walk, it is away from the office to avoid gossipy eyes/ears.

Assuming we're on the walk, after general small talk and my new job info - I'd go into saying it's been great knowing her, and if she would be interested in going out some time. Trying to keep it simple and not overthink, but would not want to frame it as apologetic about asking out of the blue - would come across lacking confidence if I said it this way I think. Either way, even if she were to say no, I would be proud of myself for even asking at all.

Thoughts? Much appreciated!

Frankly, if she likes you or wants to go out with you (provided she is single), she'll say yes anyway. Nothing wrong with your approach and very gentle. I think you're overthinking this. If she says no or is vague about an answer, take it as a no. Anything other than an empathic yes or sure! is not an agreement or showing interest. Go for it. 

[JEG88]

9 hours ago, smackie9 said:

Yes if I was asked that way it does come off lacking confidence. A confident guy doesn't leave the decision up to her, no different than asking if you can kiss her *ugh* I always got turned off by that kind of stuff...you just do it and ask her out. You don't say things like "would you go out with me sometime" lame. You say, hey would you like to go for a drink after work. There's this cool place just down the street.

Appreciate it, definitely sounds more confident since it already has an idea/initiative in mind suggesting a place for coffee or drinks. 

8 hours ago, ExpatInItaly said:

Before giving further advice, do you know for sure that she is single, OP?

I’m not 100% certain, no. But I figure I’ll never know either way, if I don’t ask. Would that change how I should go about asking her out during the conversation? 

8 hours ago, Wiseman2 said:

Stay in touch via LinkedIn.(or other social media). That way, After you formally resign and have started at the new place, you will have her contact info and can start a conversation from there. 

Don't make it awkward by prematurely "shooting your shot". If she's interested, she'll be just as interested after you resign.

No need to make yourself anxious or her uncomfortable. Why can't this wait until you are in the new job?

Appreciate the response, but to be honest this just seems creepy to me. Using LinkedIn as a way to connect for a date feels stalker-ish almost. (I don’t want to be disingenuous and feign asking to connect with her under strictly professional pretenses, since that’s not my intent ultimately.)

I understand the whole idea of not meeting up for a date until after I officially leave the company, agreed on that.

5 hours ago, glows said:

Frankly, if she likes you or wants to go out with you (provided she is single), she'll say yes anyway. Nothing wrong with your approach and very gentle. I think you're overthinking this. If she says no or is vague about an answer, take it as a no. Anything other than an empathic yes or sure! is not an agreement or showing interest. Go for it. 

I appreciate that. Sometimes I don’t read very well into the more subdued responses that might be giving off “I’m not that interested, but I’ll be nice” vibes. Either way, if she does say yes it would be up to me to give my best, most genuine impression anyway. And if it doesn’t work out after that, at least I tried.

[glows]

The simplest approach is often best. 

[Ami1uwant]

From my experience…if I might have an interest in a co-worker or someone I regularly see I will ask questions like how was your weekend, what did you do?  Ifthey were involved with someone it would usually come up in talking about what they did.

[Wiseman2]

1 hour ago, JEG88 said:

I understand the whole idea of not meeting up for a date until after I officially leave the company, agreed on that.

Nothing wrong with sharing social media. Definitely not as "creepy" as asking a coworker for their number directly when you don't even know if she ha a BF or is interested in dating you.

[JEG88]

6 hours ago, Ami1uwant said:

From my experience…if I might have an interest in a co-worker or someone I regularly see I will ask questions like how was your weekend, what did you do?  Ifthey were involved with someone it would usually come up in talking about what they did.

I like that suggestion, I will try to work in questions that might subtly reveal if she is dating anyone during our conversation. Will have to be on my game as far as not being too direct about it, but still getting at the info before I actually ask her out.

5 hours ago, Wiseman2 said:

Nothing wrong with sharing social media. Definitely not as "creepy" as asking a coworker for their number directly when you don't even know if she ha a BF or is interested in dating you.

I hear ya. I don’t post anything to social media other than work-related updates on LI, so I’m biased in terms of usage. The conversation will have to be “play it by ear” I feel like in terms of gauging a few things, not easy for sure. Thanks

[Lotsgoingon]

Really, forget about the timing of asking someone out. If you are talking in a good way with someone, it'll be harder not to ask them out than to ask them out. 

If you're having to make this huge scary leap in asking someone out, most likely the right connection isn't there.  But you do want to go on walks with people anyway. Do that more often--nothing wrong with doing that with colleagues. 

[JEG88]

3 hours ago, Lotsgoingon said:

Really, forget about the timing of asking someone out. If you are talking in a good way with someone, it'll be harder not to ask them out than to ask them out. 

If you're having to make this huge scary leap in asking someone out, most likely the right connection isn't there.  But you do want to go on walks with people anyway. Do that more often--nothing wrong with doing that with colleagues. 

It’s more my anxiety giving me fear/nerves than anything. I was also a late bloomer in my late-20s for experience in dating and romance, so still learning some things later than most now that I’m in my 30s.

I realize that I don’t know this colleague as well as I ideally would to ask her out. I’m willing to take that chance, assuming she is single before I actually ask her for a date. Not much to lose I feel like. Even if I find out she’s not single or not interested, it’d be a win in my book for learning experience and growth.

[JEG88]

UPDATE: Had lunch (instead of a walk) today with said coworker. I enjoyed it, chat was fairly surface level but flowed easily. Found out she is single. My anxiety and shyness got the better of me in the moment, and I ended up chickening out and didn’t ask her for a date. (I know, I know, feel free to criticize, I think I need that kick in the butt.)

I did leave the door open to see her again next week, saying that I would stop by before my last day. I know I dug this hole on my own, but trying to stay positive since there is still time for me to go through with it. (I tend to procrastinate as well.)

At this point, I don’t have the whole “let’s catch up!” pretense for reaching out I feel like. Will just have to man up and be more direct next time.

[Wiseman2]

4 hours ago, JEG88 said:

,saying that I would stop by before my last day.

At this point, I don’t have the whole “let’s catch up!” pretense 

Ok. When you stop by, exchange contact info. What do you mean by let's catch up "pretense"?

[letotron454]

7 hours ago, JEG88 said:

UPDATE: Had lunch (instead of a walk) today with said coworker. I enjoyed it, chat was fairly surface level but flowed easily. Found out she is single. My anxiety and shyness got the better of me in the moment, and I ended up chickening out and didn’t ask her for a date. (I know, I know, feel free to criticize, I think I need that kick in the butt.)

I did leave the door open to see her again next week, saying that I would stop by before my last day. I know I dug this hole on my own, but trying to stay positive since there is still time for me to go through with it. (I tend to procrastinate as well.)

At this point, I don’t have the whole “let’s catch up!” pretense for reaching out I feel like. Will just have to man up and be more direct next time.

Assuming you're meaning anxiety/fear of rejection, I understand what you mean. It sounds a lot more simple on paper than it really is when it comes to asking someone out. The only advice I can offer is using the fact that if you don't at least exchange information with her on your last day you'll never get another chance as motivation to make a move.

[JEG88]

Another Update: Success! Even though I stumbled through it pretty badly and nervously, I got her number today and asked her in person to meet up for coffee soon.

Now, just a matter of texting to set things up. How can I drive home the point that my intent is romantic, and not platonic? Do I just call it an actual date when I text her my suggestion for time and place?

”Hey X, it’s Y. Thanks for the walk earlier - texting so you have my number too! How about XYZ Cafe next Saturday at 11 for our coffee date?”

[Wiseman2]

4 hours ago, JEG88 said:

”Hey X, it’s Y. Thanks for the walk earlier - texting so you have my number too! How about XYZ Cafe next Saturday at 11 for our coffee date?”

Don't send this. Obviously if you text, she has the number. Also locking in an overly specific time date place is inflexible. Most people don't want to interrupt their entire Saturday for a cup of coffee. Why can't you simply ask her if she is free this weekend to get some drinks/ lunch and when is good for her.

[Wiseman2]

5 hours ago, JEG88 said:

 How can I drive home the point that my intent is romantic, and not platonic? 

Ask her on a real date. Coffee meets are for meeting someone for the first time from a dating app in order to minimize time and cost. Also asking last minute it's a good idea either. 

[Wiseman2]

On 7/28/2022 at 11:26 PM, JEG88 said:

 I don’t have the whole “let’s catch up!” pretense for reaching out I feel like. 

Why do you need a pretense?  Why suggest a coffee meet? Why ask last minute? 

If you want to date her, you'll have to ask for a real date in advance.  Not a cup of coffee on a weekend.

By playing overly casual you come across as confused rather than confident.

[ZA Dater]

My suggestion is to use confident language, being suggestive never really works and I know because I did it for years for us more shy people its easy to be suggestive because it cushions us from disappointment but the main problem is when you do this the outcome is never great anyway.

My advice is to ask her out outright and not try walk around the topic. Of course its a lot easier said than done!

[Mrin]

On 7/24/2022 at 12:54 AM, smackie9 said:

Yes if I was asked that way it does come off lacking confidence. A confident guy doesn't leave the decision up to her, no different than asking if you can kiss her *ugh* I always got turned off by that kind of stuff...you just do it and ask her out. You don't say things like "would you go out with me sometime" lame. You say, hey would you like to go for a drink after work. There's this cool place just down the street.

This. 100%

[Applejuice87]

On 7/24/2022 at 2:45 AM, JEG88 said:

First off, not trying to actively date a current coworker, per se. I recently got a new job, and will be giving my notice this coming Monday.

I've become interested in a female coworker of mine, and this change in job circumstance has opened the door for me to finally shoot my shot. (I'm a pretty introverted and shy guy with social anxiety, so this would be a fairly significant undertaking for me, as far as putting myself out there.) I worked with her at a previous company, but we've never been particularly close. We typically just say hi in passing at the office, or small talk kind of thing. We did take a walk during a lunch break a few months back to catch up as well. I do think she's intelligent and beautiful, and she seems like a good person.

I'm thinking of asking her to go on a walk again during a work break before I leave, to be able to talk to her and ask her out. I realize it will blindside her and put her on the spot either way given that we don't regularly talk, but any advice on how to transition the conversation to ask her out as seamlessly as possible? I would normally want to build upon more consistent interactions, but given my inherently limited time to ask her out, there aren't many other ways of going about it I feel. At least on a walk, it is away from the office to avoid gossipy eyes/ears.

Assuming we're on the walk, after general small talk and my new job info - I'd go into saying it's been great knowing her, and if she would be interested in going out some time. Trying to keep it simple and not overthink, but would not want to frame it as apologetic about asking out of the blue - would come across lacking confidence if I said it this way I think. Either way, even if she were to say no, I would be proud of myself for even asking at all.

Thoughts? Much appreciated!

Given I've been in this situation and was also an introvert, I just have a few words. Feel free to ignore me since I also came to this forum seeking feedback lol. In your case, it seems you don't know her that well since you say hi in passing. You mentioned you took a lunch break before - that's probably your best choice. Just it's really hard to find the right opportunity to ask someone if they want to go for a walk or a lunch break without involving other people in the office. I think the next time you exchange your "hi", just ask her if she's free next week for lunch. That's what worked for me anyways.

[glows]

On 7/28/2022 at 8:26 PM, JEG88 said:

UPDATE: Had lunch (instead of a walk) today with said coworker. I enjoyed it, chat was fairly surface level but flowed easily. Found out she is single. My anxiety and shyness got the better of me in the moment, and I ended up chickening out and didn’t ask her for a date. (I know, I know, feel free to criticize, I think I need that kick in the butt.)

I did leave the door open to see her again next week, saying that I would stop by before my last day. I know I dug this hole on my own, but trying to stay positive since there is still time for me to go through with it. (I tend to procrastinate as well.)

At this point, I don’t have the whole “let’s catch up!” pretense for reaching out I feel like. Will just have to man up and be more direct next time.

Ok, that's good that she's single and you're aware. Try again next time before you leave. Let us know how it goes.  We're rooting for you.

[Lotsgoingon]

You're being harsh on yourself.  There's nothing wrong with losing your nerve. I would say (though there are exceptions) that with a coworker, things should just naturally segue into a date if both of you have that interest.  Typically if I lost my nerve as you did, it wasn't just lack of nerve, looking back it was that the other person wasn't sending any signals of interest. 

I had a buddy at a job who I was really attracted to. Almost immediately. She and I hung out as friends, but very quickly it became clear that she and I were interested in each other. We both considered it and then pulled back--I started exclusively with someone outside of work I had met.

The point is with this person, the friend energy easily shifted to more dating energy. If the other person really likes you this way, they will make it clear (more in attitude and energy--but sometimes in direct initiative) in the same way that formally asking them out is clear. A lot of women are skilled at communicating that they want to be asked out without saying those words. One way this happens is that the woman gets close to your space as you're walking--closer than friendship distance. Or she might touch your hand or her smile might simply light you up. 

So I wouldn't stress. Any time I had trouble asking someone out on a date, there was a very good reason. Couldn't see this at the time. But can see this in hindsight. 

[JEG88]

1 hour ago, Lotsgoingon said:

So I wouldn't stress. Any time I had trouble asking someone out on a date, there was a very good reason. Couldn't see this at the time. But can see this in hindsight. 

I appreciate your insight. I think at this point, I’m trying to stay optimistic and just want to enjoy seeing her instead of having any expectations. When I was younger, I fell into that trap every time and it would just trigger more anxiety. If it doesn’t work out, it’ll be a learning experience is all. Can’t let myself get paralyzed by my own thinking.