How do you think I should ask this hostess out?

[richardwordoff]

I already have an idea of what I'm going to do, but I just want to get some feedback. If you just want to comment on my approach, then just know that I ended up having a 15 minute conversation with this cute hostess and we exchanged names, talked about our university, etc. and I want to ask her out "casually".

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A couple weeks ago I went in with a friend on Saturday and later on after we were done eating and he was still at the table I went up to the hostess and made a comment at how busy it was. I then made another harmless comment. People came in and she had to seat them so I hung around for like 30 seconds to see if she would be back. The manager came up to me trying to "help" me I just said: "No, I'm doing ok, just waiting for my friend to come on" Then I motioned to him to come on so we could leave.

Then Friday this week I went back in there, this time with my immediate family. While everyone was sitting around talking after we were done I walked outside to make a phone call and when I came back in I went up to the hostess (there was another one there but I didn't care) and made a comment related to one from last week. Then I basically ended up talking to her for about 15 minutes. At one point she went to go seat people and when she came back we continued our conversation. The second time people came in to be seated it seemed to me like she kept looking in my direction while she was talking to them. Then she got a stack of menus and nudged the other hostess to go sit this group (perhaps so she could keep talking to me, I can't think of another reason). If she thought I was weird/bothering her/whatever then it seems like she would've taken any opportunity to get the heck out of there and certainly wouldn't be getting the other hostess to seat people. Also, I noticed the other hostess dropped/threw something on the floor as if to pick on/distract the hostess I was talking to, like she knew she was having a decent time chatting with me.

During our 15 minute conversation we exchanged names (I don't know if this is consequential or not, but I asked hers and before I had a chance to offer mine she asked me what it was), talked about our university (we're both 21+ btw), majors, where we were from, etc. This is way more than I expected, especially after the 30 seconds conversation a week before. I basically kept talking with her until a couple minutes after my family left, then told her I'd better go and to have a good day. She gave me a big smile from the hostess station and (at least how I took it) an enthusiastic "you too".

I am well aware that even though hostesses are supposed to be nice to people at work. However, it seemed like she could have been "nice" and still kind of cut our conversation by giving more blunt, neutral responses (ex: if I ask her major, she wouldn't make a point to ask about mine like she did). Since this is a relatively rare opportunity I decided that I had better go ahead and go for it instead of waiting around and seeing if I just happened to see her next time I went to eat there.

I went by yesterday (day after I talked to her) around 4PM since it isn't too busy then and was ready to ask her out. I had my name, email and phone # on a piece of paper and if nobody else was around to interfere I was going to say hello and ask her if she had a second. Then I was going to tell her something like "I enjoyed talking to you yesterday and I'd like to talk to you when you aren't busy at work." Then I would hand her that piece of paper and tell her to call me or shoot me an email if she thinks she may be interested in that. If she did end up contacting me I was going to offer something non-threatening like lunch. The reason I wanted to ask her out so soon was that if I waited too long (a week or so) I couldn't really say "I enjoyed our conversation" without being weird. The reason I was just going to leave my contact information and tell her to contact me later is to avoid her having to awkwardly say yes or no while she was at work.

Anyway, she was not there, so I just went to the bathroom and left.

Today (Sunday), I am thinking about going back and trying again. However, I'm pretty sure she only works when it is busy (and on the weekends) and I don't want to ask her around other people, ESPECIALLY a manager.

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Should I just go and attempt what I described above or should I do something different?

I was thinking if I did something different I could do an approach like this:
"hello, how's it going? do you have a second?"....
"I enjoyed talking to you yesterday and I'd like you to have this"
then hand her a note that says :
"I'd enjoy talking to you when you're not busy at work. If you think you may be interested give me a call or send me an email. If not, no worries.
John Doe
555-555-5555
[email]example_email@gmail.com[/email]"
Then I would just say "well, I'll let you get back to work. Have a good day" and leave.

I'm really feeling like the approach I just mentioned would be the best because all anyone would have to know is that I told her I enjoyed talking to her the other day. For the rest she could just read the note at her leisure.

Thanks.

[Cerby]

All the over-analysis aside. I like your plan except for one thing, the note is no good, you're asking HER to contact YOU. You should go in, next time you talk to her ask her for her number. If you give her the note, you're going to sit by the phone and check your email every 30 seconds for the next month. Is that what you really want?

Don't let her have the power to contact you, just go in and ask for her number, if she says no, then you have your answer.

[richardwordoff]

Well here is my reasoning: she is busy at work. She is in a customer service position and she pretty much has to be nice to people as part of her job. If you say a couple things and slip her a note it doesn't make anything too awkward while she is at work. If I go in asking for her phone number while she is working that puts her in an awkward situation because she still has to remain nice to me. Plus, if there is another hostess (or perhaps even a manager around) the note can still work, but you can't ask her for her number in front of another hostess and especially not in front of a manager.

Anyway, I understand where you're coming from and if she wasn't at work I wouldn't even think twice about asking her for her number or just straight up asking her out to lunch. However, if she is the least bit interested won't she end up contacting you anyway? I mean, if you don't get any response within 3-5 days you can pretty much be sure she didn't give a shit about you in the first place and you should deflate your hopes of her contacting you.

[MaidenMinx]

Cerby does have a point with her saying no, but I wouldn't like to be put on the spot like that at work.

Personally I think you have your plan nailed. Please stop over thinking it.