What's the boldest way you've ever asked someone out?

I thought this random Steak n Shake cook was cute. On valentines day this year, I made him a card that said:
“Roses are red
Daisies are white
If you think I’m cute,
Call me some time”

And put my phone number.
He called the next night, and it’s working out quite nicely for me if I do say so. :)

Well, you could keep buying stuff one item at a time, and going through the line to continue the conversation going long enough to convince her you’re a safe bet, then give her your phone number/e-mail and tell her you’d like to meet her for coffee.

There’s enough cool stuff at Trader Joe’s that at one item at a time, you can talk for a long time without breaking the bank.

I believe Trader Joes sells cards and or flowers. You could buy one flower or a card or both. Take it to her register purchase it.

Move to the side out of her way. Fill the card out “Hi I am Trustinglife and I really enjoy speaking with you hear is my number. If you would like to have a cup of coffee me I would sure enjoy that. If not, consider this a thank you for doing your job so well and I look forward to seeing you each time I shop” Or something like that.

Then politely wait and when no customers are around give them to her and wish her a nice day and leave.

That is one way.

make sure you spell here right though if you go the way of Bri L

Lucky girl!

Tj’s has an awesome return policy. Take back a bottle of wine when she’s working, and say it was too good to enjoy alone. Hand her the card, wink, and wait for the call.

@ waterskier2007 – Thanks the flaw with spellcatcher and proofing your work while medicated.

You guys are sweet. And funny!

I’d love to hear it if you have any stories like generalspecific’s.
(Not really looking for advice on this question, thanks!)

Ooops Sorry Trustinglife.

Um. The boldest way I ever did was we were sitting on my couch in college. She was there with my brothers girlfriend visiting. It was the first time I had ever met or saw her. I and I thought she looked nice and seemed polite.

So when there was a pause I pointed to the “attack of the 50ft woman” poster on my wall and said “you know she is really about 167 feet”. And she said “Oh, why did you figure that out?” and I said “Sure I would love to go out, how about for coffee?”

She said she couldn’t. I said that it was ok and that the woman was probably more like 164 feet anyway. Then she said that she had to study but maybe another time. 30 min. later they called us like high school girls.

We went out the next day. Dated for a year and a quarter and she is the only other girl I ever considered marrying.

Well, I’ve never asked anyone out in a particularly bold manner, but I did kiss my first high school boyfriend in a bold manner. We were at his house watching a movie and I was waiting for him to kiss me. Well, he never did. finally, my mom came to pick me up and I had resigned myself to the fact that he wasn’t going to kiss me. So, we turned off the TV and headed towards the kitchen where our parents were. On the spur of the moment, I decided I was going to kiss him. I whipped around, said “I’ve wanted to do this all night,” and pulled his head down towards me (he was significantly taller). He was so startled that he asked for a do-over. :)

@KatawayGrey – Awesome! Good for you!! Probably just what he needed. I loved that story and lived it myself about 14 times from the boys perspective.

“Hey dude, you free tomorrow? Yes? Word. We’re going out. Here’s my number.”

YES! I have a date with asmnonet!!!!

@Bri – hehe, thanks. It was his first kiss which is probably why he was so startled.

@asmonet – good on ya for having that kind of courage!

@Bri_L: You lucky lucky boy. I’m positively enchanting.

@Katawa: I like to call it moxie. thanks. :)

Appropriately enough, my story is also about an employee of a grocery store. As a teenager, I longed to speak to the cute guy who worked in the “parcel pick-up” area. Anyone remember those guys who used to load your groceries into the car? I was too shy to talk to him, though. So one day, after he’d loaded the last bag into the backseat, I handed him a “calling card” type thing with my name and phone number on it, jumped in the car and got out of there. He called that night. We dated for a while, but he turned out to be an ass. Ah, well. It was much easier for me to ask a guy out after that, so I guess I owe him!

@ asmonet – as your icon clearly shows!
@ KatawaGrey – He was lucky to have such an understanding girlfriend!

Aw, shucks.

I kept noticing this hot guy riding a motorcycle (the bike was hot, too). So, one day I left a note on his bike that said “Hot bike, hot guy, we should go out sometime.” And I left my number. That was ballsy. But he was ballsy, too. He called me. It didn’t pan out, but it was pretty fun while it lasted.

I also met this cute boy at a record store once. We exchanged some small-talk, but they had a musician performing there so it was hard to hear. When it was time to leave, I remembered I had my senior pictures in my purse. He had mentioned earlier that we had the same phone (an envy). I took a picture out and wrote something about how, if he has his phone for the same reason I have mine he must like to text so he should text me. and put my number. He did, about ten minutes later. But he ended up living too far away for it to go anywhere.

I was passing by and there was this gorgeous girl…
Me; Hi, I’m Luiz, I’m sorry but I’m just totally infatuated with your beauty.
Girl: Hi, thank you!
Me: Do you mind if I invite you for a cup of coffee, I’m sure there si a lot more than meets the eye.
Girl: Sure, let’s go
I stopped a cab, had our coffee next day, she was my gf, after two months it was over, but it was like riding a rollercoaster :)

I told my target female that my friends bet me I wouldn’t ask her for her number and would pay for a limo if she wanted to accompany me to a formal event.
Granted, I was out with my sister and her husband and nobody dared me to do anything. The moment just felt right to take that chance.
The girl was humored by my offer but politely declined. Since then, I have been very conservative in my social approaches to potential dates, which have also yielded zero dates. Time to lower the bar a bit?

Well, I can’t say that I did the asking, but here’s a cute story about someone asking me…
I had been to this coffee shop a few times before this particular night, and I thought the guy singing and playing guitar was really cute (which is part of the reason why I kept going back when I heard he was playing). Anyway, a group of my friends and I were sitting at a table not far from the front discussing important things, I’m sure. When he stopped playing between songs he talked a little & then said he refused to play any more until the lady in the green over at that table agrees to go on a date with me. I was pretty embarrassed, but agreed. Boy was sweet, date was great, & we dated for a long while. :D

So… what ever happened with the girl at TJ’s?

Haven’t seen her since that day.

Bummer!