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I really liked my waitress and want to ask her out

Tagged as: Dating

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Question - (15 June 2011)

79 Answers - (Newest, 28 February 2012)

A male age 41-50, anonymous writes:

For my birthday yesterday we (mates and I) went to the 7 Diner, which is a place local to me 10 mins drive from here. The waitress was called Anna, and she was beautiful. She came over with a birthday cake later and sang Happy Birthday to me, and then when we left, called Happy Birthday to me on the way out. I wish I'd asked her if she wanted to come for a birthday drink after her shift!

As a way of saying thankyou to the Diner staff for a lovely meal, I wrote to them, adding 'Please show this letter to Anna as I didn't get to thank her personally, and i was wondering if she'd like to come for a birthday drink with me'.

I can't drive, walking there isn't really an option! What shall I do? Shall I ring next week or something?

(I enclosed some business cards with my numbers on them!)

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A reader, anonymous, writes (28 February 2012):

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To update you, I never heard from her or saw her again - her loss!

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A female reader, dmartin89 +, writes (8 September 2011):

No - I would say that was unprofessional.

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A reader, anonymous, writes (8 September 2011):

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In the same vein, would readers ever go out with somebody who they met at a networking meeting (could potentially be a client who you do work for?)

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A reader, anonymous, writes (8 September 2011):

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I wrote a letter to her asking if her dad was fine, and that I was disappointed when she didn't contact me (words to that effect.) My mate took it up - he offered to have me deliver it while he waited in the car, but I thought that would be too awkward.

He found out that she has a boyfriend, but he also got the feeling that if she hadn't, she wouldn't have treated me well anyway.

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A female reader, eyeswideopen +, writes (18 July 2011):

Nothing ventured nothing gained, and I wouldn't call a huge risk. You just need to shrug your shoulders and move on. It's not like you had a long relationship or anything. Course you wouldn't know that looking at this thread.

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A reader, anonymous, writes (18 July 2011):

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I think thats what I'll do.

What hurts is that I took a huge risk in ringing and asking her initially!

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A reader, anonymous, writes (18 July 2011):

This is a bit blunt, but... She is giving you the brush off.

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A female reader, angelDlite +, writes (18 July 2011):

you left your number. she knows you have been trying to reach her. she should ring you this time. if she fails to do that it is because she does not want to see/talk to/date you. she does not even give you the courtesy of a call to say ' hi what's up, i hear you have rang me' and then to either make a date with you or politely decline, maybe giving you a reason or even just a polite 'no thanks'

so my advice would be to forget this one and look for a girl who shows you is as interested in your as you are in her. if you want to give this one last shot then maybe you could send a nice card to her at the diner, write something sweet in it and include your phone number so she can call or text you, if she fails to respond to that though, you should DEFINITELY give up coz if she is not interested and you carry on it looks like stalking sorry

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A reader, anonymous, writes (18 July 2011):

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I have just rung again - she's not there today.

I really don't know what to do now, whether to write her a letter, keep on phoning until she is there or speaks to me, go up there on the off-chance, or just forget about her.

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A reader, anonymous, writes (8 July 2011):

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She won't know about dear cupid though!

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A reader, anonymous, writes (8 July 2011):

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If that's the case, why has she suddenly changed her mind?

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A female reader, angelDlite +, writes (8 July 2011):

Anna is either the QUEEN of playing hard to get or she is avoiding you coz she isn't interested in a date. She has got your number from the business card you left and she knows you have been trying to get in touch with her at the diner. why don't you wait to see if she contacts you?

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A reader, anonymous, writes (6 July 2011):

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I either give up, or persist and I shall reap the rewards!

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A reader, anonymous, writes (6 July 2011):

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I wouldn't ask Stacey out anyway!

I may leave it a few days, have one more go, then give up!

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A female reader, k_c100 +, writes (6 July 2011):

Stacey will think she is just second best to Anna and wont like that at all so she will say no, and then she will tell Anna that you asked her out and then any chance you had with Anna will be gone once and for all.

Maybe just cut your losses and move on - dont work your way through all the women working at this one place, you will get a bad repuatation.

There are plenty more women out there, perhaps look elsewhere away from this diner.

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A female reader, eyeswideopen +, writes (6 July 2011):

Piss or get off the pot. Sheesh.

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A reader, anonymous, writes (6 July 2011):

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Anna is off sick today, I am now wondering if she is interested anymore.

I might ring back and ask Stacey out!

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A reader, anonymous, writes (5 July 2011):

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It is!

I phoned back, and Aiden told me Anna isn't in today, but, unlike the others, he did tell me what time she'll be in tomorrow.

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A female reader, eyeswideopen +, writes (4 July 2011):

or watching paint dry

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A reader, anonymous, writes (4 July 2011):

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That's why tomorrow I'm going to ask for her mobile number

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A female reader, eyeswideopen +, writes (4 July 2011):

Even tho' I'm enjoying having the day off...hurry come tomorrow...this is like waiting for the water to boil.

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A reader, anonymous, writes (4 July 2011):

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Her shift finished at 2!

I am going to call tomorrow round lunchtime.

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A reader, anonymous, writes (1 July 2011):

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The last thing I want is to pressure her - I'm sticking to Monday.

I also asked my friend if ringing her at the diner would be pressurizing her and he said no.

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A female reader, CindyCares +, writes (1 July 2011):

Your friend is correct insofar if the girl had been all excited and fired up about going on a date with you, she would have asked YOUR mobile no. and taken care to get in touch ASAP:

BUT, 1) you can't blame if she is available yet not overhelmed about the date. Probably it's a much bigger deal for you than for her ,it's up to you to make her really interested in you :)

2) if she is dealing with a sick parent, it makes sense that dates are the last thing on her mind, maybe she just wants to postpone until things clear up a bit.

So, I'd say that you can give her the benefit of doubt, and assume she wants to keep your date, at a better time.

Call her again next week to ask about her dad and to reschedule, but in the meantime, do not pressure, either her or her friends.

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A reader, anonymous, writes (1 July 2011):

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My friend saw me this morning and wanted to know how I got on. I told him. When I told him, he told me that she should have asked for my mobile number when we made the date, and then when I rang the diner to ask Stacey to give her my mobile number, I should be the one that talked to her.

The bottom line (and he is a bit concerned about this) I shouldn't be doing this through a third-party, it should be direct!

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A female reader, eyeswideopen +, writes (29 June 2011):

We (and you) have until next week to think about it.

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A reader, anonymous, writes (29 June 2011):

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I will.

One question - How should I handle trying to rearrange? Obviously I am going to ask how her dad is.

Actually two questions - What if she isn't at the diner next week either?

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A female reader, eyeswideopen +, writes (29 June 2011):

How's about you post back next week and let us know what happens?

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A reader, anonymous, writes (29 June 2011):

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As I said before, she was looking forward to the date, so nothing has changed to that end, I hope!

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A female reader, CindyCares +, writes (29 June 2011):

Next week will be fine, Monday or Tuesday...

But please do relax :) This is just a date, not the planning of D-Day Normandy landings in World War II !

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A reader, anonymous, writes (29 June 2011):

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I am going to leave it until next week; I think this week is way too soon

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A reader, anonymous, writes (29 June 2011):

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What day would you say? Or is next week too early? She may be the one 'waiting' for me to ring and ask, or just may not be up to talking.

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A female reader, CindyCares +, writes (29 June 2011):

Wise decision. If her dad has a serious health problem, she won't be in the mood for socializing and flirting.Give her some space.

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A reader, anonymous, writes (29 June 2011):

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Easier said than done!

However, the last thing on my mind if my dad was ill would be a date!

I've made a decision, unless she texts or calls me, I'm going to ring the diner next Monday or Wednesday

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A female reader, eyeswideopen +, writes (28 June 2011):

Buddy you need to relax.

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A reader, anonymous, writes (28 June 2011):

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Come to think of it, when my dad and my nan were ill, I didn't want to do anything else than just be with them!

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A reader, anonymous, writes (28 June 2011):

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I've made a decision as to what I'm going to do if she doesn't call or text me.

I will ring the diner, ask for her, ask how her dad is, and if she is comfortable with it, rearrange.

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A reader, anonymous, writes (28 June 2011):

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However hard it is, I'll have to. If something (or someone) is worth waiting for, don't mess it up! and thats what I will do if I keep on ringing the diner. Unless she texts I will decide and wait for next week.

(Her work colleagues all know me now!)

Have you been in a situation like this?

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A female reader, CindyCares +, writes (28 June 2011):

Right,stay positive,anyway, it's not by worrying that you can speed up the outcome. So, either send her a card, like Freeme suggests, and let to her the initiative to contact you , or just wait about a week to give her space to attend her personal business, then call her again . But in the meantime, stay cool, distract yoursellf- don't make Anna an obsession.

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A reader, anonymous, writes (28 June 2011):

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I don't really know why she would have a change of heart as she was looking forward to it so much. Anyway, I'm sure she'll call or text

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A male reader, freeme +, writes (28 June 2011):

I know not knowing is killing you. I know how you feel. However, the right thing to do here, is to let her know, just once, that you are concerned for her, and thinking of her (in a card or note in this situation) and then for you to stay low until she is ready to respond. Don't keep checking on her. If you don't hear from her, then assume she has had a change of heart, pick yourself up, and move on.

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A reader, anonymous, writes (28 June 2011):

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This is very frustrating!

However, from what very little I know of her, she's worth it.

I got told yesterday by her colleague that she was really looking forward to it, but I understand family comes first. I have had family members in hospital, and I did not feel like doing anything else!

Also, going back to not pressurizing her, I had a bad friendship ages ago, in which I was really pressured, and it is not very nice!!

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A reader, anonymous, writes (28 June 2011):

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I think if she doesn't contact me, I will wait until next week and check he's okay.

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A reader, anonymous, writes (28 June 2011):

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If I go with the postal option, as I don't know where she lives, should I send it to the diner (for the attention of Anna)? (I don't know her second name)

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A female reader, eyeswideopen +, writes (27 June 2011):

You said earlier you don't want her to feel pressured so don't pressure her. Give it a week and then check in to say "hi how is you Dad doing?" sort of thing. Trust me you'll find out sooner or later whether she's interested.

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A male reader, freeme +, writes (27 June 2011):

I agree not to pester her, but I think showing her you are concerned is noble. Send her a card, and tell her you are sorry you missed her, and that you'll be thinking of her during her difficult time. Offer yourself to her if she needs anything. Then leave her alone until you hear from her.

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A reader, anonymous, writes (27 June 2011):

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What if she doesn't contact me?

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A female reader, k_c100 +, writes (27 June 2011):

I think you should wait now to hear from her - she will be going through a difficult time, and has got your number now from one of her colleagues so best not to pester her. She did tell her colleague she wanted to get in touch with you but didnt have your number - so I'm sure now she has got your number when she gets a spare minute she will text you.

But give her some space during this difficult time, dont keep chasing her at the diner otherwise it wont look good for you.

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A reader, anonymous, writes (27 June 2011):

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I went to the diner, and got told that Anna's dad was in hospital; she wanted to get hold of me, but she didn't have my number! I gave it to one of the other staff, and they have texted her my number.

If she doesn't text me or ring me tonight, should I ring the diner tomorrow to see if he is okay?

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A reader, anonymous, writes (27 June 2011):

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There is a pub down the road from the diner

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A reader, anonymous, writes (24 June 2011):

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Thankyou CindyCares.

Whether we come to Otford (I wouldn't bring her here to my house on a first date anyway) or stay there, I want her to feel comfortable.

I think there's a pub near the diner actually.

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A female reader, CindyCares +, writes (24 June 2011):

Do you really have to ask her to Otford ?

I'll skip that at the least at the first date.

First, she might think you have "intentions" , i.e. you want to convince her go back to your place.

Then, there's a problem with logistics, maybe you'd have to take her back to the diner , if she lives around,or closer to, there , and back to Otford again- or dump her by herself to find her way back by bus from an area which maybe she is not familiar with.

All in all, it sounds complicate, you can keep your favourite place for some other time , and on Monday just go for a drink somewhere nearer to the diner .

But try to stay calm and collected- otherwise by Monday you'll be frantic.

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A reader, anonymous, writes (24 June 2011):

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Shall I ask the taxi to wait if I ask her to Otford?

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A reader, anonymous, writes (24 June 2011):

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By the way, it is Monday at 4pm - I forgot to say the date and time

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A reader, anonymous, writes (24 June 2011):

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I don't really feel that nervous (I know it's not Monday!). Maybe it's because I've very briefly met her before, I don't know

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A female reader, k_c100 +, writes (24 June 2011):

That sounds fine - one word of advice, dont say "I thought" as it sounds like you are being too careful about what she wants to do and what she will think. Women like it when a man is organised and has gone to the effort of planning the date.

Now I'm not saying it is appropriate for this date, because you are meeting her after work. But maybe on date 2, plan a proper evening and dont worry about what she might think - be decisive and organised, they are very attractive features in a man.

I once went on a date with a guy who lived about 30 miles from me, it was the first time I had been to this town so he planned every little detail and it was lovely. He met me at the train station, he had picked out his favourite walk through the town centre to show me around, then we went to his favourite pub by the river, and then to his favourite restaurant for a wonderful meal. I loved how he had really put a lot of effort into it, and had shown me his favourite places which in turn shows his personality. It was lovely not to be asked what I wanted to do and date a man who was confident enough to have the whole evening planned.

But for your first date with her (the above wouldnt work as you are meeting her after her shift) try not to say 'I thought we could do this...' too much or ask her what she wants to do too often, women dont want to have to make the decisions all the time, especially on a first date. So word it slightly different, like "There is a great little pub where I live and I would love to take you there tonight" or something like that. It shows you have thought about it and want to show her a place that you like. If she says no, she wants to stay in the diner or something, then say "ok, not to worry, I'm happy to stay here with you, I will have to show you the pub next time". And dont sound dejected if she doesnt want to go where you have suggested - its not because she doesnt like the idea, it might just be that she doesnt want to go out alone away from the diner with a stranger (which is fair, she has only seen you briefly once) or it might be too far away from her house etc.

For this date just be flexible and dont read too much into her choice of location or what she says about your suggestions - she will have just finished work so it is not exactly going to be the best first date ever. If you get a second date that will be your time to shine.

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A reader, anonymous, writes (24 June 2011):

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I dont know whether I should say 'I thought we could go back to Otford (where I live) and have a drink in my local' if she's comfortable with that

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A female reader, k_c100 +, writes (24 June 2011):

Get a cab - getting a lift makes you look like you depend on other people to get around, that you are not very independent and you use people to be your personal taxi. Not a good first impression!

But getting a cab wont seem odd to her, it will just show that you might be planning on having a drink with her (even if you could drive, you cant drink and drive so getting a taxi would be pretty normal). Just make sure you have enough cash on you to cover taxi costs, especially if you end up going somewhere other than the diner.

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A reader, anonymous, writes (24 June 2011):

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I asked her where she feels comfortable going, and she asked me to meet her at the diner when she finishes her shift. Whether we'll stay there or go somewhere else, I don't know, but I've got to get either a cab or a lift.

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A reader, anonymous, writes (24 June 2011):

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I should actually take a leaf out of my own book.

I was friends with a girl 4 yrs ago, who tried to rush me into sex on the first meeting and then the second meeting, which I was freaked out about!! She then tried again at her house; I then terminated our friendship.

I know its not the same, but I felt pressured then; I don't want the waitress to feel pressured!

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A reader, anonymous, writes (24 June 2011):

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Come to think of it, I wouldn't feel comfortable getting calls from a girl who liked me on my mobile straight off! It would be very scary actually, plus it would put me off!

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A female reader, k_c100 +, writes (24 June 2011):

Dont get her number from her colleagues - they shouldnt really give it to you either to be honest, they should not give out personal information like phone numbers.

She needs to give you her mobile number herself, that shows that she is happy for you to contact her. If she suddenly got a call from you without even giving you her number, that would creep her out and be very off-putting, a bit like you are stalking her!

Wait until she gives you her mobile number on her own accord, until then call her through the restaurant only. You can ask her for her number, but dont ask her colleagues.

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A reader, anonymous, writes (24 June 2011):

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She's not my girlfriend yet, but she will be!

I wanted to concentrate on my education up until now.

Maybe she doesn't want to phone me because she is waiting for me (as the man) to make the next move!

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A male reader, freeme +, writes (23 June 2011):

You are 30 something and this is your first girlfriend? Wow - I understand your anxiety. I am so rooting for you dude. Good Luck. Chill out. Seriously. Be cool. I know that's far easier to say than do, and frankly I have to follow my own advice for tomorrow myself, but that's your homework, and your goal. Be cool.

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A reader, anonymous, writes (23 June 2011):

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Sorry, I am getting a bit het up, it's my first foray into girlfriends!

Do you think she would mind if I asked her colleagues for her mobile number?

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A female reader, k_c100 +, writes (23 June 2011):

Gosh if you think this is agony you really should read some of the other posts on this site, you will soon find out what real agony and real problems are!

Yes, call her tommorow, thats fine. She is allowed a day off you know, perhaps tomorow ask for her mobile number so you can get in touch with her anytime, rather than through work?

Please try and relax a bit, all you are doing is arranging a date, it is not that traumatic. If she is not around - call her tomorrow. If she is not there tommorrow - call her on Saturday. It really doesnt matter when you call her, she is not going to mind!

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A reader, anonymous, writes (23 June 2011):

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My agony continues... she's got a day off today! I was actually wondering if I should call her tomorrow, as I called her on Friday last week

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A reader, anonymous, writes (20 June 2011):

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I am going to call her on Thursday.

Thinking about it, she didn't give me her mobile number because she hardly knows me.

One of my mates told me that I am asking too many questions, just relax!

I was actually surprised that I did it, it was quite nervewracking, asking for her, but then I wasn't really that nervous when she spoke!

Also, I got told the fact she called out Happy Birthday to me on the way out of the diner was a sign that she possibly took a shine to me.

One question - on the whole, do women still expect the man to ask them out?

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A reader, anonymous, writes (17 June 2011):

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Sorry k_c100 - I think I was just panicking!

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A reader, anonymous, writes (17 June 2011):

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I'm just a bit nervous (and over-analytical!)

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A female reader, k_c100 +, writes (17 June 2011):

Call whenever you want! Are you actually being serious here? Can you not make the decision yourself when to make a phone call?

Sorry but it seems incredibly odd to me that you cannot make a simple decision such as this on your own, it is just a phone call not asking whether you should get down on one knee and propose to her! Call her whenever you have time to next week - could be Monday, could be Sunday - it really does not matter.

Look - she has agreed to go on a date with you which means she likes you and probably doesnt have a boyfriend. So just chill out, you have got yourself a date, ring her whenever you want and arrange the date, it is not rocket science.

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A reader, anonymous, writes (17 June 2011):

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I certainly didn't expect this! I took a risk and rang her, first time she was on the other line, went to work for 20 minutes - then - she picked up. SHE talked first, she remembered me straight away, she asked me whether I enjoyed my meal on Monday, I said yes, then I just asked if she'd like to come for a drink sometime. She said 'I'm busy for the next couple of weeks, but that should be fine. Give me a call [at the diner] next week and we'll arrange'!!

What day do you think I should call?

I don't think she's got a boyfriend.

Also, it stuck in my mind that she called out 'Happy Birthday' to me as I was going on Monday. That isn't telling me anything, but I dont think just anyone would do that.

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A reader, anonymous, writes (15 June 2011):

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She has heard me laugh and joke, we were the only ones in there on my birthday!

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A male reader, freeme +, writes (15 June 2011):

I think you are okay to ask her out in person, 1 time. Yes prepare for rejection, but don't go in there with your tail between your legs.

Have a bit of a plan. Talk to her a bit before you ask her out. Better yet, go in there with your mates and make sure you have them laughing. Let her see what kind of guy she is missing out on, if she says no. Then ask her out.

Attractive waitresses get asked out frequently. You gotta shine. Good Luck.

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A reader, anonymous, writes (15 June 2011):

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The postal service is awful sometimes - it should have got there today, but it might not have. It wasn't the smartest move, but you can't turn back the clock!

I think I will leave it a couple of days and ring the diner and ask to speak to her, and if she says no, I'll have to move on, if she says yes, great!

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A female reader, CindyCares +, writes (15 June 2011):

I agree with k c100 that the letter might have not been the smartest move, maybe Anna does not want all her coworkers to know who 's asking her out , maybe she likes to keep her dating life private.

Anyway, what is done is done. Sure, you can follow your friend's advice and ring her up- nothing ventured , nothing gained ! but... don't get your hopes too high up- the ball was in her court ( she had your phone nos ) and if she would have been keen I think she would have called...

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A reader, anonymous, writes (15 June 2011):

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The letter only went off yesterday so they probably haven't got it yet.

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A female reader, k_c100 +, writes (15 June 2011):

Well if its only a 10 mins drive, surely it cant be more than a half an hour walk? There is no reason not to walk over there and ask her out in person, that would be better than ringing up.

But be prepared for a rejection, the letter you sent might have creeped her out a bit. Writing a letter to say thank you for a meal is unheard of unless you are a small child who really enjoyed their birthday party. So if she did see it, there is a chance it may not have gone down too well and she may be a little bit creeped out by some random guy asking her out via a letter. I know I would be!

If you enclosed your business cards with your number, then if she was interested she would have called to be honest. But if you want to keep on trying, then walk over there and ask her out, of if you want give her a ring. Main issue is that you dont know when her shifts are - you might have to ring up a few times to find out when she will be there.

I hope this helps and good luck!

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A reader, anonymous, writes (15 June 2011):

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I was talking to a mate of mine this morning, and he said I should ring the diner, and ask for her and take a risk. Even if she says no, just thank her for everything on my birthday.

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