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When is the best time to ask someone out?

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Question - (25 June 2008) 2 Answers - (Newest, 26 June 2008)
A male United States age 41-50, *uperDan writes:

Well, I met this girl at work today. She was pretty, she was really nice, and she had an easy sense of humor (that is, I made her laugh quite a bit with minimal effort). You know, all of the good signs pretty much.

But just as I was ready to ask her to come grab a bite with me, she was already on her way out the door and my coordinator had asked me to stay behind so he can tell me about next week's agenda. UGH!

I work in a TV studio and as it turns out, she will be doing the same voice-work that I do, and just today, she ran the audio board while I directed the show. It was just us two in the control room and we had a pleasant chat, we kidded around a bit, and so on. Only trouble is we work on a freelance basis and thus, I'm not sure when she'll be in next. I'm too shy to ask my coordinator, because he's the type of person who would grill me as to why I want to know and tease me about it and such. Before long, it'd be "all around the office" as they say.

To make matters (somewhat) worse, I believe the button-up shirt I was wearing made me come off as more charming to her, except it doesn't belong to me, and I was sort of bullied into wearing it (it's a casual attire job). I'm grateful but at the same time, annoyed because it seems like anything I try on my own is always doomed to failure, but whatever this person suggests works flawlessly, and there's nothing they love to say more than "I told you so", even though neither of us knew this (or any) girl would be there today.

So anyway, my question is this:

Is it necessarily a bad thing if I don't ask out a girl I seem to connect with on the first day we meet? Also, when in your view is usually the best time to ask someone out? Because I'm starting to think that the END of the workshift is cutting it too close.

Thanks much!

View related questions: at work, bullied, girl at work, shy

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A female reader, LilzDon'tKnow United States +, writes (26 June 2008):

LilzDon'tKnow agony auntWell, when you next see this girl ask her to go for a bite to eat during lunch, and maybe getting around the office is a good thing so that way she's not as oblivious and "thrown off her horse" as you say. And try going to your friend who made you wear the nice shirt sometime. Maybe you can go buy some nicer looking clothes. Hope I helped :)

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A female reader, Artistry United States +, writes (26 June 2008):

Artistry agony auntHi there, If we could, I'd like to talk about the young lady later in my response. There is something much more salient in your letter, that I would like to address. The fact that you said, "annoyed because it seems like anything I try on my own, is doomed to failure." This may or may not be talking about this situation, if it is, then good. If it is covering a lot of situations, then the first thing you need to do is to start to reverse your thinking process, you have to believe in what you do, as a winable thing, whatever it is, create in your mind a positve thought toward

everything in your life. Positive thought, if you think you can, you will, you must believe this. If you are walking down the street and you believe you are going to step into a hole and hurt yourself, thought will become reality. Contrary to that, if you think you are going to find some money, as you walk down that same street, behold. That might be a little too far fetched, but you get my thought. You mind is a powerful thing, use it to change the negative to positive, you will do yourself a great service. Thank you. Now your lady friend. She likes you, because it seems that she is flirting just a bit, you have to increase your confidence level. The fact that she is there off and on, is a good thing, because of office romance complications, if you start dating and you break up, it could be awkward for both of you. So try ot keep it off the campus, if you know what I mean. Get her number, if she gives it to you, then you have a chance. Don't bring it to work, some places have work related rules regarding employee relationships. Just be careful. Bill Gates and his wife met on the job, and the rest is history, so discretion is the better part of valor, as they say. Good luck, but I would want you to work on thinking positively and increasing your confidence in yourself. You are talented, seem to be smart, and you are going places, just believe in yourself, and whoever you wind up with, should make for a good partner, if you take it slow and get to know who the person is and whether they share your value system. Good luck to you, take care of yourself.

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