I’m trying to build up the confidence to ask ladies out in person as online dating has been nothing but a depressing way to say goodbye to my hard earned money.

So I’m wondering if this would be an OK thing to do, as it fits only slightly out of my comfort zone (if it’s an easier and more attainable goal I’m more likely to do it).

If I go into a coffee shop, and see a girl sitting alone, no headphones in and clearly not rushed or super busy…would it be acceptable to ask if I can sit with her, as a stranger? In this scenario, the coffee shop is not packed full, and there’s ample places to sit elsewhere.

I’m thinking of either two openers:
1. “Can I sit with you, if you’re not busy that is?” And if she says yes, “I find you attractive, and I’d like to get to know you, is that ok?”

2. “Would you like some company?” And leave her alone if she says no. If she says yes, it’s a natural opening to just having an organic conversation. But I might make her nervous because I’m not making my intent clear.

What do you all think of this? Would this be welcomed by most? Or would it be creepy?

I want to come across as genuine but also not a creep or perv. I just want a simple way to allow me to talk to ladies I find attractive that won’t put her guard up too much. How do I cold approach while not making her think I’m a potential threat?

I should preface by saying I’m a big guy. 6′ 2″. 230 lbs. Green eyes, brown hair (with gentleman’s cut), jeans and a plain grey hoodie, no facial hair, decent but not perfect teeth, white, 34, male. To some, I’m intimidating just because of my size. I also tend to be most attracted to very petite girls (<5′ 2″), so double whammy of intimidating appearance. My personality is not threatening at all though, I’m pretty gentle and mot very aggressive (unfortunately my testosterone is a bit on the low side).

11 comments

  1. My personal opinion is, option number 1, absolutely not. Option number 2, better, but I can’t imagine any circumstance in which I’d be comfortable with that either. I just don’t like talking to strangers though, and when I go to coffee shops alone, it’s because I want some alone time. Please just make sure that if/when you do this, if she says no, respect her choice, wish her a nice day, and leave.

  2. #1 for sure! It’s straight forward and not as invasive as the 2nd one. But good for you for getting out of your comfort zone and going after it! Good luck!

    And even if you get rejections, brush it off. It’s still going to feel pretty liberating knowing you actually did it 😊

  5. I wouldn’t try sitting down with her. Just go up to her, say ‘Hey you’re really pretty and i’d like to give you my number if that’s okay,’ then after you exchange numbers (or not) say ‘have a good rest of your day’ and leave. lingering too long or trying to coax her into a long conversation will make women uncomfortable. keep the approach short and sweet.

  6. Usually when someone asks if they can sit with you it’s going to be because there are no other seats available. If she lets you sit with her it is not an invitation to immediately start hitting on her. You can try to start a conversation and see how it goes, but neither of your approaches are any good and come across as socially awkward.

  7. I’d vote no. That’s really putting her in an awkward spot. Unless there’s no open tables, and you literally just needed a spot to work.

  8. Option 2 is way better. Option one sounds creepy once you start hitting on them. Option two makes it clear you are trying to hit on them without coming off too strong.

  9. Omg 😳 Please do not do either of these. This is so awkward and uncomfortable to even read. I’m a huge advocate of meeting people irl and interacting and flirting like the good old days but this is so cringe. You have to give the girl an out. If she says no, she’s immediately gonna leave because she feels bad and now you ruined her afternoon. My suggestion is smile, go up to her, compliment her, leave your number for her and ask her to contact you if she’s interested and then you leave. You walk away. You both avoid awkwardness this way and you’ll know if she’s truly interested rather than possibly being just nice.

  10. no no no no no. let women go sit in coffee shops without being accosted. men really try to ruin our peace everywhere.

  11. Don’t do this. Maybe try leaving her a note offering to buy her coffee next time she’s there with you’re number on it or something. I, as a woman, would not appreciate or enjoy your selected methods, but I WOULD appreciate the offer for a potential date in a very non-aggressive and gentle way that leaves the choice up to me

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