So. Here's my email. I'd appreciate any input or edits you guys have.

Hey (Boss lady),

Last spring/summer before I started here, Jon’s boss gave us a trip to India for being at the bar for 10+ years. We had planned to go last November, but because I’d just started here, we put it off.

Now it’s coming down to use it or lose it time, and we’d like to go this November. I’d like to take the 3 weeks we’d need at the end of that month to coincide with Thanksgiving. Is there any way we can work this out? If I can’t go, I can’t go, but I’d really like to try.

Thanks,

Me

Pix, didn't Nora want both of yours? Why don't you send her both and Steph can send me hers?

Oh, now I'm confused. I thought Nora just wanted the Wellbutrin generic/brand (though I still say it's a bad idea to switch between those). I also still have Zoloft generic lying about. Nora, did you want that too? I may have missed whilst skimming.

ION, the humidity is killing me. C'mon, New England!

It's supposed to get better tomorrow, thankfully.

Here's my editing 2 cents:

Last spring/summer Jon’s boss gave us a trip to India for being at the bar for 10+ years. We had planned to go last November, but because I’d just started here, we put it off.

Now it’s coming down to use it or lose it time, and we’d like to go this November. I would like to take the 3 weeks at the end of November to coincide with the Thanksgiving holiday. Can we get together to talk about this sometime today?

Thanks,
Me

Don't put the option of her saying no in your email.

We won't be able to get together today. Today is her WFH day.

I agree with Aims. You want to be all "How can we make this work for both of us" rather than, "If you say no, it's also ok."

Most places are gonna work with you, esp. with something like this.

Go in with a plan of how you will prep your work for your absence, back up person A, back up person B, how much paid vaca you plan on having accrued by that time, how much unpaid time off you will need.

Go in with the expectation you will go, and that you will do whatever you need to do to make your absence run smoothly.

How about this in place of the last sentence?

I’m willing to do whatever it takes to make this work.

Hmm. I think that's better implied than explicit. But you know your boss, and her communication style best, so I'd go with what you think she will respond best to.

I'm not good at implying. How would you word it?

What Erin said re: knowing your boss. Like, with my boss, I could totally go into her office and say, "DUDE! Joe and I got a FREE TRIP to India!! It's for three weeks!! Can I go over Thanksgiving???" and then she's ask me for a scarf and some curry.

DJ, I have no advice, but best of luck!