I'm a 28 year old guy who's never been in a relationship and has been trying online dating on tinder, the only kind of dating I've ever tried, on and off for 4 years. I've had a handful of matches that didn't go anywhere and no dates, just three first dates that were planned but fell through.

Recently I saw this woman at my grocery store job (I'm a bagger) that I was very attracted to. I just saw her in the store and thought "Wow, she seems cool and is exactly my type". I left it at that until around a month later I bagged her groceries for her. I wanted to say something to her but I got too nervous and didn't say anything except replying to her when she thanked me for bagging her groceries.

I've decided that if I ever bag for her again and get the opportunity to talk to her again, I'm going to take it and I have an idea of what I can say to her. She has dyed hair and a cool fashion sense so I thought I'd compliment her hair, tell her that's the color I'd dye my hair if I ever do, say she did a good job with it if she did it herself, say I've seen her before and like her fashion sense and how the outfits she wears compliment her hair color nicely. She seems like she might be emo so I might ask her if she labels herself as emo and if so ask if she likes certain stereotypical emo things (I wouldn't label myself as emo but I am a guy who wears eyeliner and likes emo music and nightmare before Christmas and things like that).

But I've never asked a woman out in person before. The few times I've ever done it were over text message or on tinder, which is a little easier to do since it's just text on a screen instead of in person. Should I just ask her towards the end of the conversation if she wanted to hang out sometime, no worries if not (if the conversation goes well, that is)? Should I be direct and ask her out on a date? Ask for her phone number? Should I ask her out at all or just try to have a conversation with her and just leave it at that? I wouldn't want to make her uncomfortable, especially because she I might see her in the store again and I don't want her to feel awkward going to the grocery store because of me if she says no (I wouldn't do anything other than say "Alright, no worries, have a good day" if she did say no, I'd just still feel like I made her uncomfortable anyway just by asking).


5 comments

  1. Don’t do it man. It is not a good idea. Keep business, business. Plus she is a customer. She might freak out and complain and you might lose your job over it. No girl is worth that much trouble. I am sure there is some one out there for you. Just find her somewhere outside your workplace.

  2. Build up little chats over a few weeks and gauge the response. If she doesn’t shut you down immediately or simply acts awkwardly (important to read these signs first), then just slip her your number as she’s leaving. Best for both of you, as it gives her the initiative and also time to think about it without being taken by surprise.

  3. All your compliments/convos are good. I’d leave out the emo part tho. At the end of the convo you can just say “I would love to get to know you more if that’s okay with you” if yes, ask for number. If no, say it’s fine no hard feelings, have a blessed day and keep it moving. If she’s uncomfortable then she has the right to feel that, it’s her feelings and be okay with it if it happens. Don’t make it complicated. Be straight forward, can’t be playing those games nowadays. I hope all the best for you if you do decide to shoot your shot

  5. Gonna echo a few comments here:

    Do not straight up ask out a customer if there is no built up friendship/communication established.

    Chat with her. Actually get to know her through some small talk at your job. Compliment her hair color, sure but just leave it at that.

    But do not straight up ask her out with no prior engagement. If she is being socially pleasant to you and not trying to talk to you, it’s because you’re at work doing your job and she is receiving help from you AT. YOUR. JOB.

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