It can either be one you’ve had perpetrated upon you, or one you have inflicted on someone else…please share!
I’ll go first…it would definitely have to be the time the strolling troubadour at the Renaissance Faire licked garlic butter off my face, completely unprompted. (Long story, rated PG-13 after some serious editing room shenanigans.)
Crap - I meant to post this in IMHO, not Cafe Society, even though the backstory does involve some madrigal singing…could a passing mod please move it?
My problem is that I never know when a woman is flirting with me. Either (a) I’m alone and have no clue, or (b) my wife is with me and tells me after-the-fact that I was being flirted with by a 3rd party.
So I’m sure I would have a Weirdest/Most Random but my obliviousness prevents me from imparting it…
I run a charitable organization that feeds people in need. One day, after preparing several bags of food for a man who had just given me all the details of his life situation (recently released from jail, no money, no food, no job, no prospect of a job) he said “Hey, I noticed you aren’t wearing a ring. Would you like to go out with me?”
No. And hell, no. :wally
Seriously, was he thinking he was some kind of a great catch? I was creeped out for days!
Another time, I was stopped at a red light and the passenger in the car to my left asked me if I’d like to go out for coffee. That was more fun than the story above but still pretty random.
Well, I was in the sci-fi section of Barnes and Noble when some guy said “Nice shoes.”. He did not add the traditional “wanna f***”, but I figured that was the toned down geek version of a pick-up attempt.
I have two, and both, oddly enough, involve African guys.
The first one, I had gone to visit some friends at the college I used to attend. I was waiting for one friend to finish some meeting that evening, and so I decided to drop in and see my friend Amit. So, I walk over to his dorm, and this guy walks up to me and says hi, and I say hi back, and he inquired about what I was up to, and I said, “I’m going up to see my friend, Amit,” and he says, “Amit Lastname?” and I said, “yeah, actually,” and he says, “he’s my roommate, but he’s not home, but I think he’ll be back soon, do you want to come up and wait?” and I said okay, and we headed up. We get to the room, and I check the door to make sure that Amit’s name is indeed on it, and it was, so I went in. He offers me a beer, so I say okay, and he hands me a warm Rolling Rock from his closet. Blech. So, I’m sitting there, and we’re chatting, then he turns on some kind of Barry White-esque music and says, “you wanna dance?” and starts doing this insane, ridiculous, trying-to-be-seductive dance. So I said no thanks, and started hoping Amit would get there REALLY
Odd, I somehow hit enter too soon.
Continuing on, I was starting to hope Amit would arrive very soon. He wasn’t showing, and the guy kept pestering me to dance with him, so finally I chugged the rest of the beer, said I’d find Amit later, and ran far, far away.
The second one was about four years ago when I was working and living in downtown Rochester and I walked to work every day. I was walking along, and this elderly African guy walks up to me and asks if I can tell him where he can go for some coffee. So, I tell him there’s a coffee shop just up the street, and start walking. He calls out to me again, and I turn, and he asks me if I can show him where it is. I say okay, and walk with him down to the coffee shop, say “here you go,” and turn to leave. He stops me and asks me to come have coffee with him. I say no, I’m already late for work, I really had to get going. He keeps insisting, at one point he GRABS MY ELBOW and says “please! please come have coffee with me!” Being a complete idiot, I said fine, and went down into the coffee shop. I figured hell, he’s a lonely old guy, we’re on a busy street going into a busy coffee shop where I know all the waitresses, no big deal. So, I chug my coffee, and then I say, “okay, I really, really have to go now, I’m 15 minutes late for work, see ya,” and start out the door. He follows me out and says, “will you come have lunch with me later?” and I say, “no, I really can’t,” and he says, “yes you will. You and I will be great friends.” At this point I say, “yeah…uhh…bye.” and took off for work. Never saw him again, thank God. Creepy.
Ren Fair … walked up to a guy I found attractive and started giving him a massage. He promptly asked me to move to California with him. Then he turned around and we introduced ourselves and spent a good deal of time together the rest of the event.
Once in Mexico, while I was sitting on the beach, in the dark, with my wife in my lap, watching the ocean, I had an obviously drunk German woman stumble up to me, sit down next to me, start stroking my hair and speaking something in German. The missus was mighty startled by that, let me tell you. At first I told her I didn’t speak German (in English) so she switched to Spanish and asked me again. Startled, I responded (I’m fluent in Spanish, but how could she know that?) “No gracias, pienso que mi esposa tendria una problema con esa.” She then got up, made some strange gesture, swore at us (I think), and stumbled off. 
I can only conclude that she thought I was sitting there alone, but once she sat down and started playing with my hair there’s no way in hell she didn’t see my wife. Unless she thought she was hitting on Vishnu. 
And lest I come across as some boundless stud, I will never forget this one from college. They were showing a movie at a college-type theater near campus, and as I was in line, I turned and asked the cute the woman behind me, “So, what movie are we seeing tonight?” She looked at me, smiled and responded, “That all depends on what movie we’re going to see.” Confused by her answer I paused, but before I could speak she got out of line and walked away.
I’m still trying to figure that one out.
Well lets see…
There was the one guy who offered me a discount dinner at his restaurant. I was working late one night at Tim’s and he came in to buy some coffee with his pal.
The one guy who used the ‘You got any [Insert nationality] in you? Want some (more)?’
Those were somewhat weird, I never thought anyone seriously used the latter.
Random though… well I usually say hello to people in my neighborhood as I walk by. This was my old neighborhood. I walked past a guy sitting on the steps and eating a sandwich (I think he was one of the guys working on the roof but he was on lunch break). So I said hello and made a comment on the weather being so nice and he said “Well make sure to tell God to keep it nice, angel.” or something along those lines. Looking back it was a sweet compliment but it weirded me out a little as I thought he was hitting on me, and he looked at least my Dad’s age.
I noticed a girl staring at me, but she was with a guy, so I wasn’t sure what to think. While at the bar I ended up right next to the guy, and as tactfully as I could asked if he was with her. No, he said. “She wants to sleep with you. And so do I”. I thanked him for the flattery, but told him I was straight. I did hook up with her in a pile of leaves later that evening.
Twice in London:
My husband and I were walking Hyde Park when he decided to find a restroom. I hired a deckchair (a pound an hour) and sat down with the sodas we had just bought. One of the deckhands came up after a few minutes, indicated the soda, and said “Oh? For me?” I laughed and said that I hadn’t known what kind he liked, sorry. He asked me why I had two, and I told him that one belonged to my husband. At which point he kinda laughed and walked away. I thought it was amusing.
–
I was standing outside of work having a cigarette. Earlier in the day, on my way to get some food, a gentleman had passed me and asked to borrow my lighter, which I lent him. So as I was standing outside, having a cigarette, a guy walked by and smiled at me, but not just the normal “hey, you looked at me, now I have to smile” smile; it was more of a recognition type thing (I thought). I kinda thought it was the guy who had borrowed the lighter earlier on, but wasn’t sure, so I smiled back and he went past. As he walked away, I was kinda trying to figure out if he was indeed the guy who had borrowed the lighter. He turned back to look at me, and smiled again, and I returned the smile again, now slightly befuddled. He walks on, but continues glancing back at me. Meanwhile, he’s now about a block and a half up the street. Suddenly he turns around, and comes back. Now I’m truly baffled. He walks up to me, flashes the most heartmelting smile, and drops his gaze to my left hand. Smile vaporizes, but he tells me that I have an amazing smile, and takes off again. Obviously, he saw my ring, but it was really bizarre. He did turn back and look at me one last time before going around the corner. And he was just gorgeous.
I guess both were odd because, I’m really not used to being “approached”.
I was back in my hometown, visiting some buddies. We decided, as is our custom, to patronize the local drinking establishment. We walk in, and this scraggly redheaded drunk woman who’s probably twice my age (now to be known as Red-Headed Drunk, or RHD), approaches me:
RHD: You’re cute.
Me: Ummm… ok.
RHD: Can I buy you a drink?
Me: Ummm… just got one, but thanks anyway.
She leaves a few minutes later. So I think to myself, ok, kinda creepy, but not big deal.
Ten minutes later she returns, wearing a completely different outfit (an electric blue jumpsuit), 5 pounds of makeup, and enough perfume that the fragerance rays were visible to the naked eye. She immediately walks up to me, sits down in the chair next to me, puts her arm around me, and says what is perhaps the Worst Pickup Line Ever:
RHD: Hey baby, I cleaned myself up for you.
By this time, the entire assembled bar crowd is observing and having a good laugh at my misfortune. I quickly get up and wander over to my buddy standing at the bar, to order myself another drink. The (female) bartender approaches:
Bartender: Thank you so much for coming in tonight.
Me: Why do you say that?
Bartender: Because before you got here, RHD was hitting on me.
Me (thinking quickly): Well, I should at least get a free beer for that, right?
Anyway, after several more failed attempts to ignore the RHD, this conversation occurs (with most of my buddies and a good portion of the bar listening in):
RHD: Why won’t you talk to me?
Me: (silence)
RHD: Don’t you think I’m cu…
Me: No.
RHD: Don’t you like…
Me: No.
RHD: Do you want to…
Me: For the last fucking time, NO.
RHD: Why not?
Me: You’re drunk as hell, you’re not attractive to me in any way, and you’re annoying the shit out of me. Go the fuck away.
She then (I swear I couldn’t make this up if I tried) pissed herself in the middle of the bar and left.
Slight hijack - Using Babel Fish that translated into “Thanks, I do not think that my wife tendria a problem with that”. Maybe that’s why she was so confused
This is a little cheesy I know but I like it anyway.
Went to my bank one afternoon to make a withdraw and this is the conversation that took place with my very atractive bank teller. As she’s counting out my money to me, I was staring her right dead in the eyes as she was doing so.
ABT: “You’re supposed to be watching the money; not me.”
ME: “I know I’m sorry it’s just that your eyes; they’re so beautiful. I must of lost my train of thought there for a second.”
ABT: [blushes bright red] “Well thak you thats very sweet. You have a nice day sir.”
ME: “Hey listen, I realilze this is incrediblely forward but I’m going accross the street for a cocktail. If you’d like to join me after you get off work I’d love to buy you a drink.”
ABT: [blushes again] “Ok I’ll think about it.”
I then left not thinking anything would come of it but low and behold there she came at the pub I was at about thirty minutes later.
But alas we went out for one date and realized there wasn’t any real sparkage and decide to not go out again. We’re still very friendly with each other when I see her at the bank.
I like this story because this is the only time I can recall that I met some one outside of a bar or through mutual friends.
Actually, I think it should be “No thank you, I think my wife would have a problem with that.”
Babelfish always work better in the ear than online. 
Greasy-haired, spotty girl in cheesy pub: “Do you want to come back to my place, bouncy-bouncy?”
Mudd: “Sure.” (Gives her a cigarette.)
I dunno if this one really fits here, since I did end up going home with her.
Most random:
A friend of mine is in the Navy, and he was back on leave a couple months ago. We we’re driving to a friend’s house and stop at a light next to a woman about our age driving by herself. My buddy rolls down the window and says, “Hey, we’re going to that guy’s house [points at the vehicle of the guy whose house we’re going to] to get drunk. Wanna come?” She declines. The next block, we get stopped next to her again. My buddy asks again, this time she accepts. She comes over for about half an hour, has a beer or two and it’s really awkward.
Generally weirdest/creapiest:
Last summer I was in Australia. One night in a bar, a 30-something year old man says to an 18 year-old girl, “If my wife weren’t here, I’d fuck the shit out of you”
And…?
This may not have actually been a pickup attempt, but it was certainly strange. I was walking down the street on New Year’s Eve a few years ago on my way to a party and passed a guy who was leaning against a building. As I approached him, he stuck out his leg like he was trying to trip me. The sidewalk was quite wide there, so of course I just went around. On my way past, he yelled “Ahem. I’m trying to trip you!” I just kept going and had a good laugh with my friends when I arrived at the party.
TellMeI’mNotCrazy - when I was in London last year some guy tried to pick me up in Hyde Park too. I was sitting on a bench to take a break and look at a map to get my bearings when a guy came and sat down next to me. He proceeded to tell me his life story and opinions on everything under the sun, then moved onto the fact that he’d had a couple of Canadian girlfriends in the past, and how Canadian women are just generally superior to British women. I managed to get away before he came right out and proposed adding me to the list of Canadian girlfriends/dates, but things were certainly heading in that direction.
And then there was the mentally challenged student at my high school who decided to just take the direct approach at a school dance. He grabbed my wrist while I was dancing with a group of friends, pulled me around to face him, put his hands around my neck like he was trying to strangle me and moved in for a kiss. When I pushed his hands away from my neck, he grabbed me around the waist with my arms pinned at my side, picked me up and spun me around and around. My friends, of course, were far too busy collapsing on the floor laughing to come to my assistance, the bastards.