Asking her to buy you dinner could be misinterpreted.
Is she hot?
I’d offer to do it for free under 2 conditions:
- She was ready to go the second I said I was ready.
- She would have a Plan B in case you had plans after work.
Of course, if she were any sort of person, she’d reward you occasionally with a gift card or cash.
Are you kidding? It raises a kabillion bigger issues at the same time. She’d likely wonder what was behind that request, assume the OP was planning on making a move, and create an even more awkward moment.
To the OP: It’s a ride. What’s the big deal? If it’s out of your way home then casually say she can chip in for gas, and if it’s not then what’s the problem? I guess it depends on your past experiences, but when I lived in Austin, I didn’t have a car for three years. It’s not the most pedestrian-friendly city. When I finally did get a car, you can bet if a friend (or coworker who might become a friend) needed a ride, I was happy to oblige, as long as they weren’t taking advantage of me (see above… they pay for gas if it’s out of your way).
On preview, Pundit Lisa makes a good point: She must adhere to your schedule.
Two words… well, one of them is compound: bikini carwash.
Either that, or you get to drink tequila out of her navel every Friday happy hour.
I agree with the sentiment that she should be “ready the second you are to leave”.
There is nothing more painful that wanting to get home and having to wait another 30 minutes while she “finishes up for the day”.
I don’t know your work environment but that has always been the killer for me.
I’m leaving NOW, if you’re ready, come on, if not then see you tomorrow.
It sounds to me like her backup plan is the bus.
'Round here, the bus is 1.50 per ride. If I were getting a ride from someone, I would be a little wound up if they charged me that much, but I live about 15 minutes by by bus from work. If I lived farther, it might be more worth it. My big question is how well do you know/get along with this person? That can make all the difference in the world. Also, if you are worried about your SO, talk to the SO first.
I don’t think that your insurance company would have a problem with you getting gas money to drive someone home. People do it all the time, and I’ve never heard of any insurance company having a problem with it. I might suggest charging her half of your commuting expense, depending on the proprotions. Say you live 30 miles from work. You are now driving 33 miles home instead of thirty miles home. You pay for 16.5 miles, she pays for 16.5 miles. Assuming, for sake of ease you get 35 MPG(YMMV 
), and gas costs $2.20, she pays about $1.10 per trip. I’m talking gas only, not reimbursement rate. Your car is depreciating and wearing down whether or not she is in it. I would round for convienience and not charge her up front like day cares do (ie, you pay whether or not you use it).
Aren’t you in LA? Doesn’t your employer get benefits from SCAQMD if it has enough carpoolers? When I carpooled, I got my parking paid for and the person I picked up got $40 cash per month.
Maybe your employer is too small for SCAQMD to care about. If so, I’d recommend what everyone else has said: trial period, agreed upon amount of money, you pick the radio station. If you have any concerns on the sugardaddy front, or the people-talking-about-us-at-work front, also make it a condition that she meet your wife early on. And, frankly, I’d be up front about all of it with her. Explain why you’re asking for what you’re asking, and tell her that after the month, if it’s not working out for either of you, no hard feelings.
Alternatively, if you really don’t want to do it, tell her that you just don’t think it would work but you hope she can find someone soon.
I feel your pain. What is with that anyway? One stalled car on the 405 and the whole west side stops dead.
On the surface it may seem kind of petty. BUT if you’ve ever been in a situation like this before, you know that it can really become a drag. There is no way I would enter an open ended agreement to provide services for free. And it can’t be a casual “Oh buy gas sometimes” because it is assured that both parties will have different opinions as to what sometimes is.
Nope. Pick a dollar amount that you feel comfortable that it is worth your time (enough that it covers gas PLUS your services), propose it, and see if she agrees. You are under no obligation ot his person. I would do it for free if it was planned for only a few weeks, but open ended? Need an agreement.
If you have to question it this much in your mind I’d say forget the whole deal.
Especial since, you feel you need to make a conscience effort to keep it “business like” since the young lady in question is a fraction of your age.
Me personally? I’d do it just so I can have someone to blab to on the way home from work.
No cash necessary.
" In most cases, your liability coverage will protect you if you cause an accident while driving the car pool. But in rare instances, car-pool driving isn’t covered by your regular insurance policy. Instead, it’s considered business use of your car–especially if you receive gas money or a small fee for the service. In that case, you may need extra coverage, says Madelyn Flannagan, vice-president of research and education for the Independent Insurance Agents of America. The rules vary by company and may depend on where you live; ask your agent or company if you’re okay."
I had a drive-to-work arrangement with a co-worker once. I’d let her take my truck home sometimes because it was a horrible inconvenience for me to pick her up, particularly in bad weather.
One day, for some reason I completely forgot about her and left her at the office. I felt awful. This was a 30 mile trip. She found a ride home, but JEEZ…what the heck was I thinking?
Am I just a bad person for breaking out into howling laughter at that? How much was she paying you to pee in your car?!
I would strongly suggest that you not ride alone in the car with her, that you get others to carpool with you. Maybe I’m being overly cautious, but you don’t want any “misunderstandings” to crop up. I’m sure the Missus is a sweet and trusting soul, but you could make some offhand remark or listen to some music that may offend her and next thing you know, Carpool Gal is marching off to HR.
Better be safe than sorry. And some may roll their eyes at me, but I’ve had friends of mine accused of sexual harassment when they did nothing more than walk through the room.
I can’t remember now if it was $10, or $15, or $20 a week, for 30 miles each way. I felt so horrible, because the woman was disabled, and just trying to get an education, and it wasn’t her fault she was incontinent. On the other hand, I couldn’t stand her, and the odor emanating from her nauseated me daily, not to mention permeating my seats.
I’ll never rideshare again, unless it is with a very good friend.
Well, yeah, I feel sorry for anybody with problems like that, but you did say she didn’t take the reasonable precaution of a pack of Depends.
Am I the only one who would never agree to carpool? I think the OP is quite commendable. I like my private time in the car, though, and really don’t want anyone else taking up my time…plus there is the issue of not leaving at the same time.
You all can yell at me for being selfish. Which I am, I freely admit. 
For me that would be an inappropriate amount of time alone to spend alone with someone of the opposite sex.
I’m sure others would disagree. At least ask your wife first.
In the car? I don’t get it, how much trouble can you get into driving home when you’re at the wheel? Are you going to pull over?
Although if my SO of nine years tried to dictate who I was spending my time with to that extent - i.e., you can’t drive him home every day because he’s a *boy * - we’d be having some words!