OK - so what's the oddest way anyone has ever asked you out?

When I was in high school, I waited tables at a local Shoney’s. It was late, late one Friday night and a party of three gentlemen was seated in my section. They were real cowboy types, two older men and one young man. The young one (I’d guess somewhere between 18 and 22) never spoke. The older man seated next to him did his ordering and requests for refills. I spent a lot of time out there cleaning and refilling salt and pepper shakers, since it was so late. They were also the only people in my section. I never heard him speak to either of his companions. When I delivered the check to the table he didn’t even look at me, but when I returned the change and receipt, he handed me a napkin with some writing on it. I smiled, thanked them for coming to the restaurant, and returned to my station. The napkin read, “I love you. Will you go out with me?”

I was actually kind of creeped out. I made the manager walk me to my car that night.

Recently, I had a strange invitation for a date. First, some background: I’m 35 years old, and recently moved back to my very small hometown. I have lots of family here, but haven’t lived here since elementary school.

So, back to the asking out… I’m at the grocery store the other day picking up stuff for my grandmother, and one of the managers began chatting with me. Seems friendly enough, tells me about himself, mentions his wife. I relax after he mentions the wife – it’s not a pickup line. However, Mr. Manager tells me that his brother is single – don’t I want to go out with Single Brother? This might not have been an odd approach when I was a teenager, but it is odd two decades later! Needless to say, I politely declined.

Follow-up: I laughingly tell my grandmother about this one when I dropped off her groceries. Since then, G-mother sends me to that grocery store about every other day, in a weird and misguided attempt to spark my woeful social life.

Like Audrey Levins and others, I had more than my share of weird, gauche, and icky attempted pickups while I was tending bar and waiting tables. Only two ever worked. In one case, I was griping about the Don Juans to a fellow bartender who worked next door. He responded by grabbing me in a fireman’s carry and jogging out the front door with me over his shoulder – not a date, but a successful pickup!

Another evening, while working at that same bar, I was the DD for a regular late-night breakfast run after closing time. The breakfast “gang” (and I use the word advisedly) consisted of the next-door club owners – former Army Rangers, the previously-mentioned bartender – another Ranger, a regular customer and good friend – biker, and me. The guys got rowdy, and at some point, someone threw a salt shaker. Bad enough, but the shaker flew across the restaurant and hit a deputy in the head. I immediately started apologizing, collecting money to pay the bill, and herding large drunk guys to the car. After getting the guys in the car, I went inside once more to add more to the waitress’ tip, and to thank the officer again for not arresting my chum. The deputy asked if I’d like to eat with a more civilized crowd sometime, and we actually did have dinner a couple of times.

Thanks – but I was quoting from that particular episode, not wondering myself!

“Why don’t we get married so we will have red-headed babies?”

I’d never seen him before. He was redheaded. That was before I made my rule about never dating another redhead.

I know, so was I. That’s Jerry’s reply to Kramer’s question…

Once I started to get anonymous letters by someone who expressed admiration and compliments for me, which at first I didn’t really believe but I couldn’t understand why someone would do that. Every letter she gave some obscure clue as to her identity, but I couldn’t figure them out. One was: “I’m the one who can answer your questions.” Another was “I’m the real, beach girl (costenita).” In one letter she wrote: “When you figure out who I am, I invite you to my house for a delicious (traditional) dinner.” Finally: “My hands get cold when I’m near you.” I was going crazy, trying to figure who this was. Was it a hoax? If so, why? Could it be a co-worker? A neighbor? (which I doubted, as few of my neighbors spoke English.)

So for a couple of weeks the letters stopped, and I figured the whole thing was over. Ha ha, very funny, I thought. I was a teacher, and it was the end of the term. My last class of the day was finishing, and every one was happy because they all passed with high grades (it was an advanced class), and some students stayed after class to help me gather things up. One student walked to the entrace of the school with me, and as we were going in opposite directions, she held out her hand as we parted, saying “Thank you for the class.” I went on, and only after I’d gotten on my bus did I realize how cold her hand was.

I never saw her again.

I’m 20 now, so this happened a few years ago:

Shortly after I got my license (age 16), I visited McDonalds on an almost weekly basis. There was this girl at the drive through who I’d seen a few times, but hadn’t ever really noticed. Anyways, after seeing her a couple times, she starts complimenting my car (which was a convertibile Geo and other similar small-talk.

Anyways, a few weeks later a friend and I go into McDonald’s for a meal. The chick is working at the counter, and after I order my meal, she says she has something “special” for us, though she was looking at me. So when we get our tray, we found two free apple pies, and wedged between the two was a phone number.

As if the theme of this thread weren’t indicator enough, I didn’t call her. She was too old for me at the time (late teens, early 20s maybe) and she just gave off a creepyish vibe. Seemed like a nice girl though,

When I was 14, a guy I had been crushing on (ha!) from afar threw a phone number at me. It landed halfway between me and my friend and we didn’t know who it was for, but since I had the crush and she didn’t, I was the logical choice to call him.

When I did, he asked how I got his number. I said, “Someone threw it at me.”

He seemed very confused. “Someone… THREW it at you?!”

“Yes.”

“Oh. long pause That was me.”

Turns out it actually WAS meant for me. He became my insta-boyfriend, as things to in eighth grade.

I think that is my strangest encounter.

Sorry, I meant “as things GO in eighth grade”. :smack:

As an undergrad , I was working behind the bar at the debating union, as our regular bar staff hadn’t turned up, so I had to help out. Anyway, some really sleazy guy came upto the bar manager, and asked the bar manager if he (bar manager) would ask me out for him. Our bar manager at the time was a huge ex-rugby player, and sort of drew himself up to his full height and told said sleazy bloke where to go.

Said sleazy bloke then started stalking me. Go figure. Thank goodness for college porters who are ex-SAS Glaswegian hard-men.

Hrm … not asked out oddly but asked someone out oddly; rather, found out if he was available oddly.

I saw him stop by our office one day, so I had my boss ask his boss if they knew if he was seeing anyone, and if not, if he were interested in seeing someone.

“Hey baby…what do you say we put wings on this crate of shit and go find someone deformed who likes threesomes?”

Oh, I have to add another one, which happened (teasingly) on this board: someone who liked the fact that when he trhew me the line

“And now you know”

I would answer

“Knowing is half the battle.”

And so now we have a date (well, all in good fun) to go watch the Transformers movie.

I just find this completely charming, though.

I’ll be sure to let you know when someone manages to ask me out. :wink:

Another one! Johnny L.A. and Turtle-Man should date, IMO.

It always makes me happy to know that other redheads have this rule. I don’t want to have people mistake my boyfriend for my brother. shudder

When I was about 19, I lived in Boston, and worked about a block from City Hall. I was in front of my building, having a cigarette, one afternoon, when a guy about my age, looking typically college-grunge-chic, came up to me with a paper cup and asked me if I had any change. I said no, because all I happened to have on me were my cigarettes, and he thanked me anyway and walked away … only to come back a minute later and say “You know, I’ve got at least ten, fifteen bucks here–you wanna go to a movie?”

He was very cute, and I seriously considered it–unfortunately, I had to work an overnight, and he never panhandled from me again. :frowning:

In a Penn State dining hall a cute girl (whom I didn’t know) asked me to a Tolkein costume party that weekend. This was around '91 and there were no LOTR movies and the only Tolkein characters I could name were Gollum and maybe Bilbo.
The mental image of bunch of druids quoting Tolkein combined with my serious social retardation caused me to overlook the crucial fact: a cute chick was asking me out.

I lied and told her I was going home that weekend :smack:

Now, y’see… There’s the problem…

I was in my mid-twenties (this is 15-odd [and 15 odd] years ago), living in a weird communal house and still dawdling my college town after graduation. Starting some time in midsummer, someone anonymously left a single flower on the windshield of my car for several weeks running. I knew it must have been a night owl – it was not there the times I went to sleep at 1 or 2, and it was always there the times I woke up at 6 or 7. But I had no clue as to who this flower-leaving was. There was never a note.

At the end of this period, I was at a party and someone I did not know came up to me and handed me a flower.

Sorry to say it did not work out between us (she was adorable but too young, basically, and I was still on the rebound), but it is a charming story. Sad to say I have no idea what happened to her.

Except, “Knowing is half the battle” is from GI Joe, not Transformers.