How to ask a girl out that’s at work

First a little backstory…
I’m a 20 yr. old male who has never been in a relationship before.
I’ve always been pretty shy, but there have been periods of time (a year or two) where I just feel on top the world and have a bunch of confidence and truly feel myself.
Currently I’m feeling both lonely and depressed and I have only just realized that I’ve probably been feeling this way for seven or more years now.
I remember coming out of one of these lulls during high school and thinking, “wow, all I had to do was change x or y and I can feel myself again.”
I don’t remember what “x or y” was, so now I’m just trying to do the best I can to stay happy.
My friends and others I talk to perceive me as a very happy and quiet person, but I still don’t really feel myself.
I think I’m really down on myself when I shouldn’t be.
When I was myself people would comment on my awesome personality, but I don’t even know what that was really maybe because it was just me being myself.
Maybe I’m just overthinking everything, because I overthink a lot of things.
I can’t really talk to my parents as I believe they’re part of my problems.
My dad is trying to live vicariously through me and seems to only care about how well I’m doing in school and how much money I’ll be be making after so I can take care of him.
My mom is very negative and insecure.
They’re both always arguing about stupid things, but they’re my parents.
I live at home and commute to college and haven’t made any new friends my two years there, which is pretty depressing in itself.
I’m not really interested in drinking or smoking or I guess partying.
I’m not against it, but I just don’t enjoy it.
I have more doing other things.
I’m feeling pretty lost right now in life, I’m very good at what I do (top of my class), but I’m not sure if it’s what I really want to do as I’m really good at a lot of other things.
Anyway during my lifetime girls have flirted with me and some have even asked me out, but I just become a pile of rocks and awkwardly try and get out of the situation even if I like them too.
Recently I encountered this girl who works at the local Rite-Aid.
When I walked in with my friends we both looked at each other and I think there was some sort of connection.
She followed me from her cashier position and I think was pretending to do some work in the aisles.
She cashed me out and we had an awkward situation with my Rite-Aid card and we were both just smiling.
I left there thinking that she might be interested in me.
I went there again with my sister to get her some supplies.
I got some fruit-snacks and she let me know there was a 2 for 1 deal so I picked up another.
My sister asked why I got the same kind.
I was like there weren’t any other flavors.
She said she ate the last ones.
(We both like fruit snacks! hahaha)
It’s been about a month or two now and I’ve really wanted to ask her out and think about her like everyday.
I’m not sure if she’s still interested or was at all in the first place.
I think I should do something because I’ll end up regretting it as I have with other girls.
Should I try to start a conversation first?
It’s just kind of weird because she’s working and there’s other customers around.
Should I just ask for her number or give her mine?
I’ve thought of so many ways to to do this.
I’m also a bit worried about what to do if she does say yes, but I’m just kind of hoping things fall into place after that and I’m myself.
I appreciate you even reading through this mess and I’m glad to have at least gotten this out somewhere.

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One thought on “How to ask a girl out that’s at work

  1. Dennis Hong says:

    [Hey, I feel ya. I used to be the awkward teenage boy myself, so I get exactly where you’re coming from.

    Having said that, the first thing I want to address is your potential depression. If you feel like you have a handle on it and you just need to find your way out of your funk on it, cool. Do what you need to do. But if you notice it starting to take a toll on your life, you may want to consider counseling. A dating advice site is NOT the place to go if you believe your depression is that serious.

    Okay, so now let’s get to your awkwardness….

    Here’s the realization I came to a long time ago that helped me overcome my awkwardness around girls: You can’t think of any one single girl or interaction as the be-all-end-all. If you do, then you start overthinking how you hope it will go, and inevitably, you’ll be disappointed.

    Instead, think of every girl you talk to or express interest in as a single step towards you becoming less awkward. It’s the process of developing any skill. The only way to get better is to practice it over and over again, and also accept that you’re probably going to screw up a lot. But that’s okay. Because every time you screw up is one tiny step closer to you overcoming your shyness, right?

    Now, as far as this girl goes, given what you’ve described, she definitely sounds interested. And yeah, I get how it’s weird to try to ask her out when she’s working. So… why not write out a note beforehand and secretly hand it to her when she rings you up next time? Say, “Hey, you seem really cool, and I’d love to get to know you better. If you’d like to grab a cup of coffee sometime, give me a call: ###.”

    I think that would be the easiest and least obtrusive way to ask her out. Good luck, and let us know how it goes!

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