Do NOT STOP BY FOR A CHAT, good lord. My god. I’d get my gun if my pizza delivery guy rang my doorbell with no pizza in hand.
However, if we’d gotten to talking the last time he delivered my pizza, and I mentioned that I go swimming a lot at ___, or enjoy the outdoor music at ____, or whatever, and the next time I went he happened to be there, that wouldn’t necessarily be weird. In other words, try talking to her and see if she has any interests.
Please do not just drop in on her.
I rented a house from my girlfriend–better than I could afford without a roommate but she really wanted someone trust-worthy in it. She sent over a handyman to make some repairs and he was confident and appealing. He spent about a month getting little things done. He’d call me “just to see” how I liked the repairs (transparent but cute) and scheduled a time when he could do the roof top things. I rushed home from work to let him in and he was waiting on my porch. He had arrived on a motorcycle with no tools. No ladder. Obviously not ready to work. (transparent and NOT cute) I didn’t stop and do my usual errands and now I had to back track to get my dry cleaning and such. I didn’t see myself as out of his league. I liked him until then. Had he asked to go for a walk, to talk, to have a drink somewhere we could get away from home repairs, that would have been cool.
Don’t just drop in. Strike up a conversation. You aren’t out of anyone’s league.
It’s just occurred to me that I should go to grad school to study the sociology of nuclear physicists.
Y’all are nuts. I’ve seen so many videos where a delivery guy arrives at a big, empty house with a beautiful woman alone in it, bearing some manner of “big package” or “special delivery” with “extra sauce”. She invites him in, and invariably they are stripping down for hot, uninhibited sex almost immediately.
If that didn’t happen to you, I’d find it most unusual.
Many people don’t embellish the idea of dating their pizza guy. But the porn industry seems to have a penchant for the delivery-guys-bangs-lonely-housewife(gayboy?) thing. So, maybe there’s that.
Of course, I don’t relish the thought of garnering a date from someone I’m buying food from, either. Then again, I don’t consider the car dealer, banker, general contractor to be first-line sources for my dating pool either. That’s what the internet is for, am I right? =P
Just be cordial, mention that you’re sorry it took so long as you were studying for grad school or something. It’s personal, but not so personal as to make one think “um, shoo”. Like, don’t start off with “Man, you’re some hot chick, wanna shag?” It’s possible to be entirely professional, a bit casual and still within the realms of propriety. G’luck!
You should. You might consider going to the University of Cardiff to learn from Harry Collins, who has been studying the sociology of physics for decades.
Yeah, I didn’t think that last post through properly. “I was in the neighborhood” might well be more stalkerish than cute.
But my intent was to say that I think that the OP is making a bigger issue out of the whole deal than it needs to be–it’s just that it’s hard to find an appropriately casual way of meeting someone when you already know where that person lives.
I have to admit, I’ve not had a delivery person try to pick me up, but I’ve been hit on by guys in cars or trucks before (I was a pedestrian), and frankly it did make me feel more nervous about walking straight home than flattered.
I know the porn jokes have already been made, but have you seriously considered the possibility that it isn’t “dating” that she’s interested in? I don’t mean in the sense that she wants to jump you before you can put down the pizza, but if you’re single, and she’s single, maybe she’s looking for some fun with a cute guy sometime.
I’m not necessarily suggesting you act under any such assumption; I just didn’t get the impression you were looking at it from that potential angle.
I like the idea that a guy who has seen me in my weekend lounging-around clothes and hairdo is still interested in me.
This situation has never happened to me, so it’s hard to say, but I definitely don’t think it’s out of the question.
Assuming this even goes this far, but are you prepared to date a single mother with two children? If you’re not, then you’re really doing her a disservice by getting involved with her.
I’ll third Anaamika and Velma. I don’t really think there’s an appropriate way to ask her out.
A few years ago I used to frequent my local independent video store. There was a clerk that worked there that I would chat with when I went in - he seemed nice and was pretty knowledgeable about movies. One day he pulled my phone number from the store records and called me to ask me out.
I would have had no issue with dating a video store clerk, had I not been living with someone at the time. But the fact that he used his position to find out my number and where I lived totally creeped me out. I’m sure he was a nice enough guy, but I thought what he did was inappropriate. I turned him down, and I stopped going to that video store.
In my mind, the fact that you’re delivering food as a job is less relevant than the fact that you’re in a quasi-business relationship with her and know where she lives. She might be uncomfortable having someone who comes to her house to perform a service displaying a romantic interest in her, and she’d probably feel put on the spot were you to ask her out.
That only happens when the pizza delievery man arrives only to discover that he’s forgotten to put on his pants.
[Having not read the entire thread.] Yeah, the OP is a food delivery guy, but he’s a food delivery guy going to grad school.
I.e., potentially a great catch. Maybe there is a super-subtle way to drop this info in a 5 second chat.
What say you, ladies?
Of course ask her out. Ask her for something simple like coffee or a drink
This “I’m not good enough,” is ridiculous.
Whether it’s a job or physical appearence, so what? She says “No,” the world won’t end.
Go to the wedding license bureau you’ll see fat guys with knock out girls, ugly women with handsome men, this like only goes out with like doesn’t hold up. I’m not saying it’s entirely true, but there are too many exceptions.
She might not want to marry you but so what? You can date, heck you might not like her.
If she says “Yes,” you buy her a drink, if she says “no,” you say “thank you.”
And then you come back here and tell us about it. 
Ladies, would this situation be slightly different if it were the UPS or FedX guy?
Well, UPS and FedX guys tend to make enough money to live on. I don’t know any pizza delivery people who can say the same. Still pretty icky to ask someone out when you’re delivering food to their home.
No. Nor if its one of my vendors at work who drives a BMW and makes $100k+ a year. Nor if its my financial adviser. Or my doctor. For me, it isn’t a money thing, its being accosted on a personal level while making a business transaction.
Also there is something about a guy you barely know who has a ‘thing’ for you who knows where you live. Not all men have good boundaries and a lot of women had that college experience of the guy who’d hang around in the hall outside her dorm waiting for her to come back from class (I’m talking about you Mark) that creates at best an uncomfortable situation where you most want to be comfortable (your home) and at worst a threatening one.
Nope. I might prefer to date A UPS or FedX guy over A pizza delivery guy (not that my own present employment status entitles me to job-related snobbery)–but the real issue is the business relationship, coupled with the uneven playing field–delivery guy knows where she lives, she knows only where he works (and what he looks like).
her first and last name (she probably doesn’t know his at all), what time she tends to be home, approximately who lives in the house with her, whether she has a large aggressive dog…
Not all women are paranoid about things like this. But a lot of us are - if not paranoid - made uncomfortable.
I was asked out by the guy who works in the Greek/Lebanese food kiosk at the mall.
I’d go in there about once a week and he always slipped me a few extra stuffed grape leaves or something-- little freebies. One day, he gave me his number.
I was completely squicked out and never called him and did not go back to that restaurant for a good six months. I just went back a week or so ago and he wasn’t there. Thank all the gods.
My issues: 1) He is Middle Eastern and his English is spotty. While I have no problem with that at all, in a casual relationship or in a business transaction, I couldn’t see myself discussing the finer points of Nitchze vs. Kierkegaard with him. 2) He works in a restaurant, which means he probably works a minimum of 65 hours a week. When, exactly, was I supposed to see him? Would he be taking weekend vacay getaways with me? Nope. He’s the guy who always has to work and can never do anything. 3) How many other customers did he give his number to that week?
I’m just relaying how I thought about the situation from the woman’s point of view so you can avoid sending the messages that squicked me. And remember, just because there’s no ring and no man around doesn’t mean A) She’s not still married, but separated, or B) She doesn’t already have a boyfriend.