I used to regularly get rides home from a coworker. My house was “on his way” and he drove and parked downtown. I never paid him, he never asked me to, but I used to bake a lot and give him the results. He is still a friend.
I never had him stop by the store. We worked the same hours and both of us hit the door at quitting time, so I didn’t make him wait for me, nor was his schedule likely to vary. I think he enjoyed the company (as I said, we still go out to lunch a few times a year, even though we have to drive a few miles to see each other). I had a boyfriend - who never said anything at all about my carpool buddy. (I have a lot of opposite sex friends, particularly work buddies, I work in a male dominated field).
If it didn’t work for him (like when he went on vacation), I’d take the bus.
Biggest pitfalls I see…
This is a door to door deal. If she ever says, even once, “can’t you drop by the grocery store, I want to run in and get milk” the answer is “no.” (Unless you get to be friends and this is the exception and something you want to help with). People can take advantage, and setting boundries is appropriate.
This really only works if you both have the same hours. I work with two married people who carpool, and when one needs to hang around the office so the other can wait, it can build some resentment - even when they are married and/or good friends.
Most people, I believe, are reasonable, and understand that you will go on vacation, put your car in the shop, may change circumstances (hours, move), or switch jobs. I’d only worry about being considerate enough to give notice when you can.
Bonus points for you if you can give the true translation; 19 times out of 20 I see it mistranslated, always with the same mistake, and that mistake is not trivial to the meaning.
I’m leaning towards not asking for the money. It’s not an everyday thing anyway, as it turns out. And she just told me she got me a bottle of wine for my birthday, which I had inadvertently mentioned in reference to a DMV appointment. So it’s probably better to keep things on a friendly and informal arrangement.
It’s a tiny bit awkward nonetheless; she seems to toss out the compliments more than I am used to getting from the opposite sex, but that’s probably just her.
Tell someone in HR that you’re carpooling with this person, esp. if they gave her your name. That way someone at work knows about this arrangement and no one can say it was on the sly. Also, rather than ask for money, agree with her that when you go for gas after work every other week, she can chip in if she wants.
Maybe she got you the bottle of wine to butter you up to give her a ride… doesn’t mean she’s hitting on you. It’s possible that she is, of course… but letting all the appropriate people know about the situation (your wife, your work) will probably be all the protection you need in this situation.
But there is no indication that the the OP’s spouse is uncomfortable with it: "On the other hand, if I do ask, that helps keep it on a businesslike setting, always something to think about when I’m married and this woman is probably about two-thirds my age if not half. "
Spectre of Pithecanthropus :“Shame on him who thinks this evil”
And as with just about every situation like this throughout time you will be made to wait. This is why I don’t get involved in this kind of thing. At some point she will get held up and so will you. Then you’ll feel guilty about telling her down the road that you don’t have time for this.