When EVERYONE Is Out Of Your League...

In My Humble Opinion
1

I’m mainly looking for female opinions here.

I’m 38 years old, and soon to be (in September) a grad student. For the past few years, while doing college, I’ve had this dumb food delivery job - A customer orders from a restaurant, the order gets dispatched to me, I go to the restaurant and pick up the food and take it to the customer’s home. Kinda like glorified pizza delivery, but I like to think I’m better than the pizza guy, 'cuz as an independent contractor I don’t have to dress like a clown or put one of those stupid signs on my car.

So tonight I took a delivery to this woman’s house, third time I’ve been there. She isn’t a total knockout, but I find her to be quite attractive; I would guess she is about my age, maybe a year or two older. She has a couple of young kids, but I’m pretty sure she’s single:

Each time I’ve been there, I’ve seen no sign of a man about.

Tonight, she said she was ordering food because of her “usual Sunday laziness” - I’d think that since she felt compelled to give me a reason, if there was a father about she might have mentioned that, as it was Father’s Day and all.

I did my best tonight to take a look at her hands, no rings.

The first time I delivered to her, she seemed kind of flirty to me - but I’m too thick-headed about women to notice these things as they’re happening. I only realized it with hindsight. But then again, being a dumb guy, perhaps I thought that because I was attracted to her. The second time she wasn’t as flirty, but tonight she seemed so again.

Anyway, I doubt I’ll ever act on my attraction, but I’m curious: if I were to consider it, would I be deluding myself? I mean, she lives in a nice house, brand new, larger than average, in an above-average area; I assume she owns it, but I suppose she could be renting - either way, she must be doing well for herself. And who am I to her? The food delivery guy. Yeah, I’m a real winner - I’m sure she’d jump at the chance to go out with me!

2

Someone needs a hug. :stuck_out_tongue:

Whoa, hold up there fella - not me, I mean you, :wink: and maybe she does too. You never know until you try. You’ve got some things going for you - you’re single, educated (soon to graduate, I hope) and employable in a well-paying job (I hope - need more info).

But keep in mind that lack of confidence can be a real turnoff, so don’t bring up your current crummy job situation unless she does. She knows what you do anyway, so if she says yes to a date focus on the positives you’ve acheived.

3

I’ll tell you what you DON’T do. You don’t deliver her a pizza and then later that night text her with “Don’t be mad but I think ur kinda sexxy! Want to go out?” and then, assuming she didn’t get it the first time, resend. Because not only was my boyfriend on the couch but, like, ew!

Next time you deliver to her, try talking to her. I mean, not too long, because the food’s getting cold, but if she stays out on the porch to hang out with you for a few minutes, that might be a good indication.

4

Some people have a naturally flirty personality.

I’ve always thought it really squicky when someone I’m attempting to do a business transaction asks me out, but I’m strange that way.

I’d go with Zsofia’s suggestion of trying to chat with her for a few minutes and see if she holds up her end of the conversation. If she does, and a few minutes chit chat is interesting, then you both have the perfect excuse to continue the conversation when you don’t have other deliveries to make. “I’d love to keep talking, but I can’t keep my other customers hungry, maybe we could chat sometime I’m not at work?”

5

^^^^^^^

Second this approach.

6

I agree with Dangerosa in principle but I’ll be painfully honest and say - yah, I’d never even consider dating my food delivery guy. I’m sorry. I know it’s shallow. Everyone has their moments of shallowness.

That doesn’t mean I wouldn’t necessarily date a food delivery guy, although that might be difficult too. But I’d be more inclined to try if I met him first and then found out what he did. But not my food delivery guy, not ever. (And it would definitely help that it was only a “temporary” job. I’m actually not as judgemental on jobs as I seem to be coming off. I just don’t mcuh like food service jobs, I guess.

Also, I guess I’m with the “financial transaction” thing…we’re in a business relationship, I’d rather not take it anywhere else.

7

While the issue of some people being weirded out by dating someone they have a business transaction with could be a problem, I can verify that some of us females are definitely willing to consider guys who make less money.
I was a medical student (I’ve since become a physician) and my boyfriend was a security guard making minimum wage when we first met. I knew the odds were that I’ll always make more money than he does, but I wanted to start dating him because I thought he was a great guy who was intelligent, honest, and attractive. Our different jobs have never caused trouble for us and we have a very strong relationship. Some women may place a lot of importance on finding a rich guy to date, but it is definitely not universal.

8

Well, yeah, I don’t care how much money he makes, but my pizza guys see me in my pajamas with bed hair all the time. Not hot sexy bed hair, either. I prefer to think of them as sexless automatons, so I don’t have to put a bra on.

9

I’d casually mention grad school if an opportunity comes up. That might make her consider you more of a social equal.

10

I’ve only ever dated a guy who makes more money than me once. He was a total jerk. I’ve dated several guys who had no job and that sort of sucked but we got by. Not all women are looking for a gold mine.

Besides, wouldn’t it be terribly romantic for a woman to fall in love with you while you’re “just a delivery guy” and then still be in love with you when you’re a PhD or whatever? That’s pretty special!

11

Reality says that you shouldn’t make a move on her from the position of her delivery guy.

If she knew more about you, and she could identify you as just someone who has been thrust into a particular situation; and she was the type that admired how people conducted themselves once thrust into a particular situation; and she developed respect for you; and she noticed your confidence and ability to step above this temporary station in life, then you might want to act on your desires.

Or, you just might want that super-rare gem of a successful, above-average woman who doesn’t care that you deliver food door-to-door, and you might think that it’s time to play the Powerball version of dating, wherein you make a wager that has 178 million to one odds.

Anything possible, but it’s best to determine how realistic it is.

12

I’m confused— don’t these situations usually result in the woman not having enough money for the tip, pondering “some other way” to repay you, and dropping to her knees as funk music kicks in from somewhere? Or have I been misled?

13

It depends. When you peer into the house through the front door, is there, like, a lot of fake wood paneling?

14

“All I really needed to know, I learned watching porn.” I think it will be a best seller…

15

Are you going to keep this job when you start grad school? Because if you don’t, you could start saying things like “It’s nice seeing you on my route – I’ll be sad when I have to give it up to start grad school.” And even if you’re not sure you could say “I hope I have time to keep this job **when I start grad school **in a couple months. The money’s good but I need something in my field.” And of course she will ask you what your field is and you’re off to the races, impressing her with your proposed thesis in nuclear physics or the sociology of wharf rats or whatever.

16

Yeah, I agree with this. The problem is that if she is just a friendly person, and you ask her out and she says no, now there is awkwardness. I wouldn’t like being asked out by someone who is serving me in any business capacity for that reason because now I would feel like I couldn’t order from that restaurant anymore (should I tip him extra now? Will he take that as a sign of pity or encouragement, etc.)

It is not that I would never consider dating a delivery person, just that when someone asks someone else out, that moment should be when both people are set up as equals. It is weird when someone has just given you money (or is about to) and you ask them out.

17

I graduated in March, B.S. in Math. I’ve been trying to find a better job, but there isn’t a lot out there for my degree; besides, I don’t want to get into something full time, what with grad school starting in a few months. And, what I’m doing pays well enough that I can work part time and afford to live alone, and has great flexibility for working around school… I’m probably stuck with it for the next couple of years.

I didn’t mean to imply a lack of self-confidence, though I can see how I might have come across that way. I’m just trying to be realistic.

18

We actually work with over 100 restaurants in the metro area, so you’d never be able to order food delivery again. :slight_smile:

And, this is why I doubt I would ever act - the awkwardness factor. When else would I ever see her? As it happens, she lives less than two miles from me, so I suppose there’s always a chance I could run into her somewhere else, but I’m not holding my breath.

19

Agree with those who said it’s not dating a food delivery guy that’s weird, it’s dating your food delivery guy. I would feel very skeeved out turning someone down who knows where I live (and possibly that I’m single with children). I think many women have been on the other end – getting asked out by a regular customer while working at a bar or store. Same sort of situation in that he knows where to find/stalk you and any future business transactions will be awkward.

Just enjoy the flirting. And Sigmagirl’s suggestion is pretty good, though it may be a bit transparent. Which may be endearing. Oh, so many variables in the language of love!

20

If she lives less than two miles from you, you could walk, or ride your bike or otherwise contrive to be “in the neighborhood” and stop by for a chat.

This technique is most likely to be effective if you can have some expectation of her being outside in the yard, so you don’t have to actually ring the doorbell to start a conversation.

Also, I suppose there’s a certain amount of risk factor about the potential risk of looking like a stalker.

But I’m generally with others who suggest that there is nothing wrong with your credentials as far as potentially getting a date, but that the time to try is not the same time as when you deliver food.