It's a tough thing to ask somebody out, but these people below have figured out the smoothest way to do it.

Below are 22 stories of the smoothest way a guy has asked out a lady. Check them out!

1. Summer of sophomore year, there was an ice cream store I would go to religiously every other day. It got to the point where I didn't even have to order. I'd just walk in and he'd have a cone ready for me by the time I reached the register. Finally, one day he says,"You really like ice cream."

Me:"Haha yeah, I do!"

Him:"Do you also like pizza and a movie? Maybe...Saturday?"

Me:"Actually! My friend Naomi and I are going--" (Friend elbows me hard and conspicuously) "--not going. Anywhere. See you Sat?"

Him:"Cool. I'll see you here, usual time." Then he gave my friend double scoop on the house.


2. Him: bubble tea is gross.

Me: Ugh bubble tea is the worst.

Him: We should go out for bubble tea, and not order bubble tea

Together for four years.


3. We met at college. We started hanging out after some friends introduced us and he told me about D&D. I'd never played so he said he would teach me the rules.

One night after we'd been hanging out for a few weeks we started talking about relationships. He told me about some ex-girlfriends, then he asked me about my past relationships.

OK, so my back story at that point was 0. 0 boyfriend's, 0 guys kissed. No one had really seemed interested and to be honest I was pretty insecure about it. To add to that I had been on my first date ever about a month before I met him and the guy bailed when he found out I'd never been kissed.

But I wasn't the type to lie so I told him.

His response was a thoughtful "Hmmmmm" and then he leaned forward and kissed me!

Then he said "There, problem solved!"

We've been together 15 years, married 13 years and have 4 kids.....And he's still the only guy I've ever kissed!


4. We had a class together and started talking about two weeks before it ended. I thought he was cute as hell but didn't think he felt the same way.

He and his buddy lived the same way I did and on the last day of class, they walked home with me but split paths after a few blocks.

So I'm walking and kinda gushing to a friend via text about him and I hear someone running and it's... (Continued)

So I'm walking and kinda gushing to a friend via text about him and I hear someone running and it's him! He tells me that he'd be a massive idiot unless he gets my phone number because he thinks I'm super cute.

We've been together for three years.


5. I was bartending. A customer I had a few good conversations with asked me what time my shift ended, and I told him 2 AM. He leaned back and said, "Can I order a coffee? I'm going to need it if I want to stay up until 2 AM."

Note: I don't want to be harsh, but bartenders are paid to be nice to you. Be 105% sure someone's into you before you pull a move like this.


6. I met my husband in a BDSM club. He was spanking me and said "Your butt looks a little sore. I have an ice pack back at my house."

Been married for four years in November.


7. At one of my old labs, there was a job where you work with a partner who has to print numbers on these little plastic cases for you to put samples in. You're doing it for hours, so it gets really boring, but you've also got to concentrate, cause if you mix up the numbers then two patients could get each other's diagnosis and you could kill someone. The advantage of this job is that you can basically talk to the person you're working with for hours, because eventually you start doing the checking subconsciously (sort of like driving and talking to someone at the same time).

Anyway, I'd been getting close to this cute new guy for a few weeks, and we'd been hanging out all day just shooting the breeze at work. Right at the end of the day, as he's handing me one of these cases, my subconscious alarm goes off telling me the number on the case is wrong. This happens pretty often, hence why we're so paranoid checking, so I pick it up to hand it back to him and ask him to reprint it, when I realise it's his phone number he's printed on the case. Look up and see him smiling the most confident grin I've ever seen in my life.


8. I snagged my wife of 8 years with...

"I have an 8" telescope. Want to come over, have some dinner and drinks...look at the stars?"

She immediately drove from Texas to NM. She was genuinely surprised I was... (Continued)

She immediately drove from Texas to NM. She was genuinely surprised I was actually talking about an 8" telescope.

I've been disappointing her ever since!


9. So, I was in a pre-dental program at my college and one of the requirements was a class with all the different premedical students about applying to our actual dental, medical, veterinarian, etc schools. There was a guy who sat behind me in that class and we always bickered back and forth. So at the end of the semester we have to get up and give presentations with the other people in our grad programs. Dental went the first day, and this guy was in the misc. group who went the next day. He gets up to start the presentation and hands out the outline for their topics but he runs out just when he reaches me. I'm annoyed thinking he's just mess with me. He goes to his bag and pulls out an extra and hands it to me. So after like twenty minutes I get to the last page of their outline and I see the last line says "Lunch?" And I look over at the person sitting next to me and their paper. Sure enough, it doesn't have that extra line. I looked up at him and he winked. It was hands down the cutest way I have ever been asked out.


10. In grade 8 a guy friend of mine came to my door with a plastic watering can. He opened with "John told me that you have to make it memorable when you ask someone out, so I brought you a watering can."

SUPER CUTE. I definitely will always remember. I said yes. We dated for 2 weeks and then both concluded we are better as friends, but it was still the best way I've ever been asked out.


11. One Saturday morning there was a knock on my door. I opened it and there was a young guy my age with a construction vest in. He stared at me for a couple seconds and I said: "Can I help you?"

"Hello! We are doing some work on the pipes on this street...." he was basically telling me I couldn't flush the toilet for a couple hours while they did the work.

A couple hours later, they were done and gone. I had to run some errands so I went to leave. Stuck in the door was a note asking me out.

It was signed: "The guy who told you not to flush".

Maybe not the smoothest, but one of the cutest ways I have been asked out.


12. I was at a party with a friend of mine when this guy comes over with a deck of cards. He insisted on showing my friend his "party trick" and proceeded to have her choose a card at random. She grabbed the card and kept its identity to herself and he placed it back in the deck and shuffled it. He started laying down cards and ended when he reached 10. He looked up at her and said "Do you notice anything interesting about these cards I laid down?" She shook her head and he then looks her directly in the eyes and says "it's... (Continued)

She shook her head and he then looks her directly in the eyes and says "it's my number, call me." He then proceeded to give her an over exaggerated wink, shot her some finger guns, and disappeared into the crowd of the party.


13. He came into my chocolate shop everyday for a week on his break and we had fun random conversations about life. On Friday, he came in looking a bit disheveled and I was genuinely concerned; asked him if everything was okay. He looked at me with the most vulnerable eyes and said, "would you please let me take you on a date tonight?" It was so upfront and honest. He wasn't trying to conceal any emotions or hidden agendas. He gained massive points in my book for that one.


14. I met a guy when I was like 16 at a convention; we happened to be in the same area and really hit it off talking about art and drawing. We started doodling each other while still chatting away, and exchanged portraits when it came time to part ways. He signed his drawing of me with his phone number.

For two nerds at an cosplay convention, that was pretty damn smooth.


15. When I was living in Boston there was a really cute guy who would play his guitar and sing in the stations along the blue line. I always gave him a few bucks because he was really cute, and he was really talented. He'd smile and call me the girl with the yellow roses (I have tattoos of yellow roses on my back), and then I'd get on the train and be gone. I was (still am, actually) in a long-term relationship but I figured it was just harmless flirting.

After about a month and a half of this I walked into one of the stations. I could hear someone playing ukelele. And then I heard "hey, girl with the yellow roses!" so I looked around and saw him, sitting on the bench with a bouquet of yellow roses, and he started playing "My Girl" by The Temptations, on the uke. When he was done I walked over and he asked me out for coffee. It was so cute (albeit a little embarrassing because, crowded station) and if I had been single I would have said yes. But I didn't. He smiled and said "aaahhh, that figures. Have a great day, pretty girl!"


16. Not a girl, but proud of myself for this one. This one time in university I had a crush on a girl. We were friends/acquaintances, and photography was one of my hobbies. She asked to go on a photo excursion so we walked around and took photos, and I snapped a few of her doing some funny poses. I had the photos printed, and gave the ones of her to her, but on one particular one I wrote on the back that I thought she was cute and that she ought to let me take her on a date.

She said no. Oh well.


17. Walking through a crowded train station my eyes met with a man talking into his phone. Not looking away he said "Sorry, something's come up." snapped the phone shut and walked straight over and said hi. Hands down the smoothest thing ever.


18. At a party in college on a roof a boy jumped down from a higher portion right next to me and said "You're the most beautiful girl at this party. Can I have a cigarette?" And we were together for two years.

But I think the best part was in the middle of our first date. He said "can I just get this out of the way?" And then bam! He kissed me.

I found out later it was an Annie Hall reference. And he asked me out because he has a fetish for a certain type of nipple and could tell by looking at me I had that type.

What a weird two years.


19. I had just met this guy at a friend's party and we instantly hit it off. I was telling him how I have a really bad relationship with coffee because it gives me the craps. At the end of the night he said "I'm facing a dilemma here because I really want to ask you out but you can't drink coffee and you're not old enough to get a beer, so like, tea? Would you like to go out for tea?" Relationship didn't last long but granted it was the sweetest way I was asked out.


20. I was at a party with this really cute guy that I had been talking to for a bit. I didn't really know anyone there though so I wanted to go home, and his friend was way too drunk so he ended up giving us both a ride home. Anyway, he dropped me off first which I was kind of bummed about because I was planning on making a move once his friend left but I assumed he did it on purpose and wasn't into me.

Not 10 minutes later I get a call to come downstairs as I'd left something in his car and he wanted to give it back to me. I get downstairs and ask what it was and he just put his hands on my face and pulled me in for a kiss. He asked me out but I had basically melted at that point and I think I just nodded and grinned like a fool. Definitely the smoothest thing a guy has done.


21. I just went through an ugly breakup when these happened and these boosted my confidence when I really needed to still feel like I was an attractive person:

1) I was on a bus in DC on my way to meet a friend at the Phillips Art Gallery (making myself go out and do new things). I met the gaze of this guy a couple of times, both of us one of the few not glued to our phones. I had put in quite a bit of effort into looking nice but still just felt awful and low. When I got off the bus it had started to pour. I was desperately trying to find something my purse to cover my head when the same guy walked up and opened his umbrella over both of us, smiled, and asked, "How was your day?"

2) I was at my coffee shop (you know it's yours when you frequent it often) and a guy sitting across from me asked me if I knew the wifi password. I told him the password and thought nothing of it. He was cute but I wasn't interested in starting a conversation (still feeling down). I got up to go get a sandwich and was kind of bummed when I came back and he was gone. I sat down and noticed a note on my keyboard that simply said, "You're distracting." With his name and number beneath it. That one was very flattering.


22. This was at our local bar. I usually would go by myself after work to read. Some find this weird, but I actually find it a lot easier to read outside of my house, and I was reading the Sandman series for the first time. A good friend of mine also lived in the neighborhood and she'd meet up with me sometimes. My friend is very chatty and chummy with the regulars, I prefer to keep to myself.

I had noticed him among the regulars, thought he was handsome, but didn't really care that much. Lots of handsome jerks in the world, I don't feel the need to talk to every one of them.

One day he approached us with a crossword and asked if we'd care to help him. My friend said sure because she's nice, I said sure because even though I'm not nice and didn't want to talk to some guy I didn't know... I did kind of want to do a crossword.

We work on the crossword, my friend helps for about five minutes, gets bored, goes to talk to some other regulars, we finish the crossword and chat once we're done.

He then made sure to bring a crossword every day, and continued to ask for my help.

After a couple of weeks of doing crosswords, he walked me home (he lived two streets past me from the bar), we kissed, I went on a weekend trip and when I got back and saw him again, he just said "let me take you to dinner."

Almost three years later, we still do a crossword almost every day.



You May Also Like
Hi friend— subscribe to my mailing list to get inbox updates of news, funnies, and sweepstakes.
—George Takei