Best timing on asking a woman on a date?!

[musicman777]

Hey everyone,

Part of my daily routine is I go grocery shopping late at night (mostly because of my work I am a late night dweller)! There is a girl that works there and I don't see her all the time, but I think she is pretty cute. Finally I seen her working tonight and I made up an excuse to pick up something in her isle and I started talking to her (something I would have been TERRIFIED of doing a long time ago but I am starting to get more comfortable talking to women \\ I made a comment about her working late and asked her name and introduced myself! I left it at that for today but I was pretty proud of myself for going that far. It went pretty good as well, she had a bright smile on her face when I started talking to her and I felt some good vibes from her.

 

I absolutely AM going to ask her on a date but now I am just trying to get the timing down! I thought it might be awkward to ask her out on a date out of the blue on the first conversation. I thought it would be better to get her to know me once and start thinking about why I may have introduced myself that way and see if there was any initial chemistry (which I think there was). Now it's just the timing. Should I ask her out next time I see her our talk to her regularly a few times, like 3 or 4 visits to get to know her a bit more?

 

I don't like to stall and dwell too long on one girl, then find out she has a boyfriend or something stupid or isn't interested. She seem to knew I was a regular, so it's not like I am walking in off the street late at night looking for someone to hit on. Any opinions from ladies on here? Should I just go for it the second conversation or span this out some? One difficult part, she doesn't always work, I think she is part time. Lastly I kind of feel that regardless of the number of visits if she finds me interesting enough she will say yes even in the second conversation.

[greta96]

Why not try to incorporate a coffee invitation into your conversation next time you see her? See how the conversation goes, and take it from there. If let's say she's busy with customers or the conversation doesn't feel like it's flowing the right way, then you can hold back on extending the invitation and you can always do it the next time you see her.

It's not like you have to put your life on hold until she tells you yes or no, you can go about your life as normal, and whenever you have the chance to ask her, you ask her. No need to rush.

[TMifune]

It's always iffy to try to pick up a girl where she works. A lot of people just aren't in the frame of mind to really think about that while they're working. Servers particularly. Since their pay is based on being nice it's really hard to read the situation.

 

I'd say the timing is less important than making it a really casual invitation so it just doesn't seem like a big deal. That way if you don't get an immediate positive reaction it doesn't have to be a big deal. Something that makes it clear you're interested but doesn't put her on the spot too much or leave her feeling pressured.

[Feast]

Yeah TM nailed it about making it a casual invite. I've asked out girls at their work before, it's ok, if it's casually done. Maybe just saying something like "after I spoke with you last, I thought to myself I should have invited you out for coffee or dinner. Would be fun..." That's enough to get your point accross, see if she helps you out from there. If girls like you they'll help you out after you first drop the hint you want a date. Sometimes they freeze and get nervous, that's not necessarily bad. Give them time to respond. I remember a girl I asked out really liked me and I didn't know it and the way she responded was scaring me off but she was just nervous.

 

I suck at this too, just figure out what you want to say in advance, that helps me.

[Man with Dog]

Say about 3-4 conversations before you ask her out. After that you could get friendzoned permanently. I've asked girls out at their place of work. I once noticed a much younger girl turn round when she recognised my voice and it was obvious she'd noticed me before. I was friendly but as it happened after I married and my daughter was born, I did not ask her out.

 

Another girl who worked at a restaurant I'd been to could remember everything I had eaten and drunk. It seemed almost stalkerish.

[j.man]

I'm someone who draws a big, bold line between work and social, so I've never really considered asking a woman out at her work.

 

But if I were to in this situation, I might come in late when there aren't any lines, shoot the **** while she checks my stuff, and when she hands me the receipt, write my number on it and give it back to her with something simple like "Let me know if you'd like to grab a coffee sometime."

 

There's no way to avoid it being an awkward situation for her, so you want to do it in a way that puts her on the spot the least. Making it quick, writing your number, not asking for hers, and not posing the question in a way that she would feel obligated to answer right would help a lot, I think.

[SoulTaker]

It's always iffy to try to pick up a girl where she works. A lot of people just aren't in the frame of mind to really think about that while they're working. Servers particularly. Since their pay is based on being nice it's really hard to read the situation.

 

I'd say the timing is less important than making it a really casual invitation so it just doesn't seem like a big deal. That way if you don't get an immediate positive reaction it doesn't have to be a big deal. Something that makes it clear you're interested but doesn't put her on the spot too much or leave her feeling pressured.

 

I agree with TM. It has to be super casual. It's a situation where she has to deal with you (work), and be nice to you as part of her job. The last thing you want is to come on too strong, she rejects you (negative), and then dreads having to deal with you every time you come into the store.

 

Best, for you to have a few more conversations in order to see what type of vibes she gives off (and if she's available). If a woman is interested in you, she'll let you know with either positive energy, or in subtle ways. Also, understand that this is her job, and she has to be careful in dealing with customers (who have been known to "go off" on workers who reject their advances).

[SophieGrace]

Seems like everyone is advising you to go for it. I agree. As for an approach, I'd link it to her work, "I know you're working, but I'd love to continue this conversation. Any interest in getting coffee sometime?" Then you can give her your number, or she may proffer hers.

[musicman777]

Hey everyone,

Thanks for the replies! It's not so much her being at work as much as the timing I was just worried about that. I can see here no one really seems to think that is a huge issue! In fact one of you mentioned the "friendzone", definitely want to avoid that! That is one good reason to move on her sooner rather than later.

 

A lot of your are commenting on her about being at her job. Her being at work isn't that big a deal to me honestly. I don't get out that much in the day due to my job, these are the kinds of people I normally run accross in life. Just because they are working doesn't mean they are unavailable or don't have a personal life. I see nothing wrong with asking them out as long as I am respectful about it. Everyone is fair game! I recently asked a girl out that works in a coffee shop (that story is on a another thread from a couple months ago) and she is very open about it and actually wants to do it. Her life is VERY complicated however and she can't really date me anytime soon (she "promised" sometime this year and it is impossible to make her move any quicker). I recently heard some advice from someone, "life offers no guarantees" and in case things don't work out for her, well, I am not hitched to her, so I am looking and asking other girls out!

 

There are "red flag areas" for me for women that won't work. I won't ask out a waitress, bartender, or someone that works along those lines. The coffee shop was a unique predicament and the girl became very familiar (and chatty) with me. But people that serve/cook food and deal with a lot of people don't take any request like that serious because they always hear it and usually I don't go for those targets. This girl I am interested in, she stocks the shelves in a grocery store. She's not dealing with tons and tons of customer interaction or anything. She seemed very friendly and had a nice smile on her face when I talked to her, I had a good feeling from it.

 

I appreciate the feedback. I am going to be casual about it as well, I do want to try to make it clear its a "date" though!

[JustWishing]

I think you should "go for it" too. Next time you see her, try to casually converse with her. Preferably when it is not that busy, so that her attention is more on you. Maybe throw in a compliment about her appearance, hair, eyes, clothes she wears, earrings...whatever and then say that you like her personality and if she wants to hang out sometime for lunch...coffee...ice cream...Your choice on this one. Then see what she says If she is in a relationship ...at this point she would most likely tell you if she has a boyfriend, if not she might just go for the date

[musicman777]

Hello everyone,

I asked the girl out today and she made it very clear she has a serious boyfriend already. Story of my life, last four people I asked our have boyfriends, getting sick of this bs.

[Man with Dog]

Hello everyone,

I asked the girl out today and she made it very clear she has a serious boyfriend already. Story of my life, last four people I asked our have boyfriends, getting sick of this bs.

 

Well at least you won't be spending the next 50 odd years thinking "what if". You could ask if she has any sisters. I actually know a couple who got together that way! The girl was attached, so introduced him to her sister.

[TMifune]

Hello everyone,

I asked the girl out today and she made it very clear she has a serious boyfriend already. Story of my life, last four people I asked our have boyfriends, getting sick of this bs.

 

It's hard to risk rejection like that. All you can do is try. You did good.