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I would love to ask this waitress out. Any suggestions on how to handle this?

Tagged as: Crushes, Trust issues

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Question - (14 June 2016)

63 Answers - (Newest, 14 July 2016)

A male age 41-50, anonymous writes:

I like a waitress in the town near to where I live.

She has served me on several occasions, and said hi and spoken to me. I would love to ask her out, but my bottle always goes!!

It was my birthday yesterday, and on the way out she said 'Have a nice day. See you later.'

She was wearing a ring, but not on the correct finger (second nearest to the thumb) on one hand and a thumb ring on the other. These days though, women wear rings, no matter if they're single or taken!)

I am going in tomorrow for lunch with my sister (as she wasn't here for birthday.)

Have you got any advice for me?

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A female reader, CindyCares +, writes (14 July 2016):

Of course you can do it .We had no doubts about it.

I must say that I see it somewhere halfway between Andie and Serpico.

I.e. : while I don't think the Macho Man approach is necessarily the winning one, and personally I don't like guys " who walk into the party like they walking onto a yacht " (... I hope somebody is old enough to get the reference :) I understand what Serpico means. If you had asked her , the first time "so, do you want to come for coffee Sunday night ?" ( not... some time... one of these days )... and, in case she answered: no I cannot on Sunday, you had said " Ok , Monday then ;" or variations of this dialogue.....

You would have kept things simpler, faster and REAL.

She would have to come out and say: Yes, or not. Yes, great , it's a date, or- no, no way , in your dreams pal. She would have had to take a stand.

She would not have had the time or way to think of a polite brush off, ( the boyfriend, which must be fictional, otherwise she would have mentioned him immediately ) thereby , in practice, giving you the runaround.

You see, the problem is that many women aren't used to be assertive, and to call a spade a spade, they want to be nice, not hurt feelings, etc.... so, if you let them, they 'll reject you with a series of " dog ate my homework " excuses hoping you get the hint or get fed up. Which may be a longish process.

This girl, too, you have to consider that she is your server , - she may not want to risk pissing off a good customer- so she basically bought time until she could come up with a reasonable, non offensive excuse : a boyfriend, true or fictional.

Not such a big deal, in itself. As you say, you did it once, you can do it again. Plenty of girls around. Consider her good practice in the art of asking girls out :)

What I find a tad worrisome, is not your having been rejected once - that's normal- - eh, you can start worrying maybe at the 50th rehection or so .... What makes me think, instead, is that apparently you are not great at reading signals. Verbal and non verbal clues, body language.

You said she looked KEEN ! Now, from uninterested to a little interested, it may be a fine line, it's hard to say at times. But from uninterested to KEEN ?..

Maybe it's just lack of experience, though. The only way to learn to read people... is to meet ,and interact with, plenty of people, and keep doing it until you get the hang of it.

Best luck next time, don't worry.

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A reader, anonymous, writes (14 July 2016):

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At least now I know I can do it!

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A reader, anonymous, writes (14 July 2016):

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Thankyou for the advice. I didn't wait outside terrified and reheared it as I went in with some friends, so I just went in like I would on any other day.

However, I will bear that in mind for next time.

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A male reader, Serpico +, writes (13 July 2016):

OP -

For starters, I give you credit for finally asking. The more you do it, the easier it will get.

Now for the other side of the coin. Given your tone coupled with everything you have said, I don't believe for a moment you went in there "confident." I know this simply by the fact that she turned you down. I do believe you waited outside terrified and rehearsed what you were going to say and finally walked in. I do understand that, but know she sensed this in a New York minute. Notice how when you first brought it up she was going to make you "wait two weeks," and now somehow she "has a boyfriend."

My point is not to beat you up, but rather to have you learn something. Gaining confidence with women is often a learned skill. What I can tell you is keep asking, no matter what the results. At some point, you will start to have a familiarity, comfort, confidence, and swagger that women fall for on the spot. I can tell you this with certainty because I was you early in my life. I did the same exact shit you do, and with the same results. Slowly my game and confidence increased, and by my 30s there was hardly a single woman who turned me down when I approached and asked.

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A reader, anonymous, writes (13 July 2016):

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At least it has shown that I do have the courage to go up to a girl and ask her out!

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A reader, anonymous, writes (13 July 2016):

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Thankyou

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A female reader, Andie's Thoughts +, writes (13 July 2016):

You approached her the right way, OP - don't worry. There's absolutely nothing wrong or inferior about the way you went in there :)

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A reader, anonymous, writes (13 July 2016):

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I did go in there confident.

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A male reader, Serpico +, writes (12 July 2016):

Once again, the way you went about almost assured she "had a boyfriend." This is EXACTLY what I warned you about below, and lo and behold played out precisely as I expected.

If you went in there confident and presupposed the date, 99.9% chance you'd been out with her at least once already.

Nothing you can do about this now as she already sees you as a beta, but dont make the same mistake twice.

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A female reader, aunt honesty +, writes (12 July 2016):

Oh well the thing is you tried and you should be happy you had the confidence to do that. It is a shame she is already taken but there are plenty more women out there.

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A reader, anonymous, writes (12 July 2016):

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Went in last Thursday with no expectations. She was in there, and I reminded her about asking her the time before, however, this time, she did tell me she had a boyfriend!

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A reader, anonymous, writes (30 June 2016):

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Ok, I'll try and forget it until next week, otherwise, as you said, it won't feel spontaneous. The nature of my job requires me to put a lot of cheques in my bank, and that is opposite.

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A female reader, Andie's Thoughts +, writes (29 June 2016):

You're still overthinking it. If she's not in, wait until she is. Don't go in more regularly than you normally would because it's kind of obsessive.

If you go in once or twice a week, just keep doing that, don't go in three or four times. Don't stray from what your normal routine is; this is a first date *opportunity*, not set up, but the more you plan it, the more you're setting it up, rather than letting it happen naturally.

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A reader, anonymous, writes (29 June 2016):

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What should I do if she isn't on duty the day I go in?

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A female reader, Andie's Thoughts +, writes (29 June 2016):

Not all men and women are the same, though. Many couples are shy or just don't like being "presupposed". A lot of us like more consideration or contribution from both people for the first date and so on.

This isn't just what I'm saying, this is what I'd do; I'd be intimidated or at least uncomfortable by someone coming up to me saying something like "Friday night, 7pm, ______" because that's who I am.

Not every woman likes being *told* when/where/etc. Many women like it or are okay with it, but some of us just really don't like it.

Stop overthinking it, OP.

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A reader, anonymous, writes (29 June 2016):

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Ok, I will try - it is hard though! What do I do if she'd not on duty when I go in?!

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A male reader, Serpico +, writes (28 June 2016):

Edit -

I think I need to put an addendum on my last post. When I say cocky, confident, and arrogant, this is absolutely something you cannot fake. Women will smell this out in a second and you will be nowhere. Its arrogance, but its CALM arrogance. Notice I didnt say walk up and say "YOU'RE GOING OUT WITH ME FRIDAY!" Its more asking the question very calmly, but with the intonation that you are presuming the answer already. The same with saying "I cant wait that long" regarding the two weeks. You don't say it nervously or angrily. IF you need an example, imagine how Sean Connery as James Bond would say it. Said with that intonation, the woman will melt on the spot.

Last - Andie - notice I didnt DEMAND a date and time, I presupposed it. VERY big difference in the way a woman views it from a man. Demanding it shows weakness and a lack of other options. Presupposing it shows strength and an abundance of other options.

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A male reader, Serpico +, writes (28 June 2016):

With all due respect to the ladies here, Im not going on what woman SAY, Im going on what they DO. Ive lost count on how many women have told me they want a "nice, confident guy," and then go home with the biggest a-hole in the bar.

To be honest, I dont even think many if not most realize they are doing it, but the fact is, almost all of them do.

The empirical data I cannot dispute is when I acted nice, open, and accomodating, I was consistently turned down or given the "boyfriend" excuse. When I became cocky, arrogant, and demanding, I was consistently successful, and with women far better looking than those that turned me down in earlier years. Ive had many friends who've had the same exact experience.

NEVER listen to what people SAY, ALWAYS watch what they DO. This is one respect in which men and women are exactly the same.

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A female reader, Andie's Thoughts +, writes (28 June 2016):

You're just overanalysing and takin the fun out of it. Stop twisting yourself into different "what do I do" questions - you said it yourself; "what ifs" drive you round the bend, but so does this. You're obsessing. Forget about it until the time has passed, then go in and ask again.

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A female reader, CindyCares +, writes (28 June 2016):

Personally, but I think many women share my preference, I don't like arrogance but I like confidence. It may be a fine line.. but it exists.

OP- it's just a date. You are asking for some of her time, not for one of her kidneys. No need to twist yourself in knots over this. If she sounded keen, most probably she'll say :OK, day "X " sounds good.

If instead ( just in case. You know, expect the best, prepare for the worst ) she changed her mind, - accept that and move on. Think :" Her loss , not mine ".

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A reader, anonymous, writes (28 June 2016):

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So Andie, if you were this girl, and I asked for you (like she's ask me to do) what do you think I should say, and what would you say?

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A reader, anonymous, writes (28 June 2016):

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That's what I thought Amanda, and the whole object of this is me wanting at least a follow-up! I do see where Serpico is coming from in a way, but I think if I do that, it will have the opposite effect.

Any more thoughts?

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A female reader, Andie's Thoughts +, writes (28 June 2016):

I'd find it obnoxious if you demanded a date and time, so I'd turn you down. Not everyone likes the type of alpha Serpico describes - many do, but a lot don't.

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A reader, anonymous, writes (28 June 2016):

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Serpico, that can either go one of two ways can't it? Some women don't like arrogance! And if I go in next week, ask for her, and TELL her we're going out, that may have the opposite effect?

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A reader, anonymous, writes (28 June 2016):

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Any other comments from the others who gave me advice?

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A reader, anonymous, writes (28 June 2016):

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Good advice.

Well, as you said she agreed to go out with me, so I will take your advice, and she'll want a second date!

I wish I'd said last week I couldn't have wait two weeks, but I cannot turn back time, so I shall have to wait until next week, and then go in and sweep her off her feet!

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A male reader, Serpico +, writes (27 June 2016):

OP -

To answer your question - back in my younger reserved/shy/whishy-washy days, women I asked out ALWAYS had boyfriends. Then, in my later assertive/confident/cocky days, women I asked out NEVER had boyfriends.

Funny how that happens ...

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A reader, anonymous, writes (27 June 2016):

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Didn't get that answer Serpico!

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A reader, anonymous, writes (27 June 2016):

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Thankyou Cindy.

Although two weeks from last Thursday isn't until next week, so I've got a while yet!

I think because she said she is working for the next two weeks, some men may ask 'What if...?' but that only sends you round the bend!

Question - if she had a boyfriend, would she still have accepted? (sounds strange, but it does happen I think!)

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A female reader, CindyCares +, writes (27 June 2016):

I agree - no need to fake " keen ".

I did not mean to jinx your date, OP :). It's just , that you know how they say : Expect the best. Prepare for the worst.

Best of luck !

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A male reader, Serpico +, writes (27 June 2016):

My primary advice at this point is to stop letting her set the agenda/schedule for the date. I cannot overemphasize how much women like men who are assertive and can take charge.

She already agreed to go out with you. Go in there with a plan/time/date in mind, and TELL her that's when you guys are going out. When she first said "two weeks," you already missed a golden opportunity. If a woman said that to me, I would have calmly responded - "Thats great, but I cant wait that long." She would have loved it, and be damn sure she'd have found time somewhere.

Stop being so uncertain and wishy-washy with this. You keep up that course of action, you'll be starting another thread here on "I dont know what happened." Again, be assertive and confident, and she'll fall over herself to be available for you, in more ways that you can imagine. Be wishy-washy, and get very ready for "the friend zone."

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A reader, anonymous, writes (27 June 2016):

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I will - thankyou.

I'd like to think she meant business.

I'd also like to think that if she had a boyfriend, she would have told me she was busy and given me the polite brush-off (and also she wouldn't have told me to ask for her next time I'm in I dont think)

She sounded quite keen actually!

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A female reader, CindyCares +, writes (27 June 2016):

I'd follow the program and do what she said : next time you go to this place , ask for her and remind her your coffee date. If she meant business, she will arrange with you a day and time . If she was tryng to let you down easy ( alas this can happen too, maybe she can't afford to be too blunt with a regular customer ) she will come up with ifs and buts and reasons why she is not ready yet . At which, in doubt, you give her ONE more chance to reschedule, and then, if she does not take it, that's it. Mission not accomplished- move to the next.

But that's of course just a worst case scenario. If she said : ask for her , then... go ahead , ask for her :)

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A reader, anonymous, writes (27 June 2016):

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Let me edit that a bit!

She said next time I go in (in a week and a half) ask for her and we'll arrange something.

Any advice?

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A reader, anonymous, writes (23 June 2016):

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Well, that was unexpected!

I went in there, she was on duty. I sat down at the table with a couple of friends I went in with (I didn't plan to go in there just to see her, I had to put a cheque in the bank, otherwise it would have seemed a bit desperatue!)

I saw her outside having a fag break, was undecided as to whether to go out and ask her. I plucked up the courage, asked her if she got the note I left with one of her colleagues last week, she said no! I then asked if she'd like to go for a coffee, and she said yes! I gave her my business card, which included my number. She said she is working for the next 2 weeks, but after would be lovely.

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A reader, anonymous, writes (23 June 2016):

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I'll do that today, and hope that she's on duty!

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A female reader, aunt honesty +, writes (22 June 2016):

I really feel that you have over complicated things for yourself, really asking a woman out should not be this big off a deal at your age. You are an adult, and yes it takes confidence to ask someone out, I do understand that, but I think you are over thinking everything, just go in and ask her does she want to catch a cup off coffee with you some day.

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A reader, anonymous, writes (22 June 2016):

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Thankyou Serpico - good point!

No, I don't know if she got the card, so if she is there tomorrow when I go in, how should I handle it? (or am I overcomplicating things for myself!)

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A male reader, Serpico +, writes (22 June 2016):

Leaving a business card is a bad idea - it shows you don't have the balls to ask her face to face. Women like confidence above all things.

You actually blew your chance when she said, "See you later." If that were me in your shoes, I would turned and calmly said to her - "Why don't we make sure of it. Would love to take you out Friday."

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A female reader, boo22 +, writes (21 June 2016):

By the way I forgot to say, how do you even know she got your card?

You said she wasn't on duty, anything could have happened.

Whoever picked up the card may have forgot about it or binned it by mistake.

That's happened to me before.

Never assume x

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A female reader, boo22 +, writes (21 June 2016):

Hi OP,

Of course it's flattering to be asked out whether you go out on a date or not.

Everyone I know likes an ego boost even if the person who asks isn't your cup of tea.

I've had crushes on customers. One guy for nearly twenty years and I've tried everything lol.

I gave him my number on a sticky note that I kept down my bra in readiness in case he came in.

When that didn't work I got his number off someone else and text him. That didn't work either.

It's become a joke now with him and his colleagues and me.

If he calls someone when I'm there he always sends his love and I tell him I'm still crazy about him.

Take your ego out of the equation. She may have a boyfriend so if thats the case then all this has been for nothing.

Guys that have asked me out in the past and I've declined tend to give my restaurant the swerve for a while and then everything is normal and life goes on.

You'd better let me know what happens ?? .

Go for it x

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A reader, anonymous, writes (21 June 2016):

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I have got to go to put a cheque in the bank this week so would it be the perfect opportunity to go in and see her?

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A reader, anonymous, writes (21 June 2016):

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I did take your advice boo22 - she has got my number now. Ok, maybe I didn't do it in exactly the way you said, but she has. I will say something (carefully) when I go in next.

As a waitress Boo22, did you find it flattering to be asked out?

Andie, I see your point as well.

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A female reader, boo22 +, writes (20 June 2016):

Hi again!

I think everyone here is over thinking this.

I've been a waitress for 25 years and this is no big deal.

I wish you had taken my advice the first time. You've made this hard for yourself. You will probably know instinctively what the score is when you first see her next time.

There's nothing wrong with asking someone out if you do it in a nice way. At least you didn't have to be drunk to do it.

She should at least be flattered. Be light-hearted about it and you'll be fine x

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A female reader, Andie's Thoughts +, writes (20 June 2016):

I don't really know; it's hard when you don't know anything about them and have no common ground to bring up. I guess you say something about wanting to go for coffee? Personally, I don't think you should, as it could be seen as creepy for asking with no real reason to other than her looks. Like, really, what *can* you say? :/

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A reader, anonymous, writes (20 June 2016):

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Any advice on what to say to her next time I go in?

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A reader, anonymous, writes (17 June 2016):

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Thankyou Andie, wise words

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A female reader, Andie's Thoughts +, writes (17 June 2016):

Dating is about getting to know the person, but you normally know something about their personality already that makes you want to know more - right now, all you have is her looks and age, as well as that she's a polite waitress. I'm not saying that's necessarily a bad thing; you should still ask her out (and I think it's wise to wait until you next go in for a meal), but you're currently only wanting to date her based on physical things, which is just something to be aware of when asking her out.

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A reader, anonymous, writes (17 June 2016):

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Isn't the whole point of dating getting to know the person? And to the person who asked me to ask her if she got the business card, I am not going to go in there just to see if she's on - I will find out when I go for a meal next time - otherwise it might look a bit desperate!

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A reader, anonymous, writes (17 June 2016):

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No it doesn't, well, it would do if she was under 25!

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A female reader, Andie's Thoughts +, writes (16 June 2016):

Does her age have anything to do with it for you? I'm only asking because you don't really know anything about her to want to date her personality.

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A female reader, aunt honesty +, writes (16 June 2016):

Maybe you could ask her did she receive the business card that you left her and tell her you would like to take her out, if she refuses, then the best thing you could do is avoid eating there for a while, but if she doesn't hopefully it all goes well. Good luck.

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A reader, anonymous, writes (16 June 2016):

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I'm 37, I have, but not much, she seems guninely nice.

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A female reader, Andie's Thoughts +, writes (16 June 2016):

How old are you? I know this may not seem important, but it could be because it may affect my advice. Why do you like her? Have you had a conversation with her? Why would you like to ask her out?

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A reader, anonymous, writes (16 June 2016):

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She is about 8 years younger. I have left a business card with a note on the back; when I go in next, shall I ask her?

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A female reader, aunt honesty +, writes (15 June 2016):

I don't think leaving a note is a great idea at all, it is always best to ask face to face. Practice in the mirror if you must, but keep it simple, ask her what time her shift finishes as you would like to take her out for a drink if she is interested.

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A female reader, Andie's Thoughts +, writes (15 June 2016):

How much younger?

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A reader, anonymous, writes (15 June 2016):

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I asked her out on the back of a business card as she wasn't on duty today!

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A reader, anonymous, writes (15 June 2016):

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She's younger than me

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A female reader, Ivyblue +, writes (15 June 2016):

I agree, ask her. Worst case scenario she says no and you find somewhere else to eat. I cant see any thing wrong with a good ol' fashioned line of:

" I'd really like to take you out some time, how about ( insert date ) if you are free?" Good luck. Nothing ventured nothing gained my friend!

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A female reader, Andie's Thoughts +, writes (14 June 2016):

How old is she?

If she's about your age, go for it. Though, "Have a nice day. See you later" is what they get paid to say to everyone, so don't think anything of that.

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A female reader, boo22 +, writes (14 June 2016):

Leave her your number on the little tray you get with the bill with a nice message then leave with a nice smile.

Good luck x

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A female reader, singinbluebird +, writes (14 June 2016):

Just ask her out! lol

She is giving you the green light and probably wonders why this cute guy that comes in every once in a while hasnt made a move yet.

Go for it =)

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