My Bridesmaid might say no, should I ask first?

I would most definitely call her beforehand. Also, while the proposal boxes are fun, you can totally call your other people and ask too without the boxes, it just adds a lot of pressure to say yes, especially when everything is personalized.

You would be fine calling her beforehand and if she says yes, maybe send her a gift but not necessarily a proposal. It's nice that you're considering her position as a new mom!

I would send the gift without telling her.

Thanks, Susan! I'm in Houston!

Skype is a great idea! More personal than a call, but still less pressure.

Alforev, I like the idea of a gift instead of a proposal!

You can always ask them all first, then send boxes to those that say yes.

My bridesmaid got pregnant after I asked her- she is due TWO WEEKS before the wedding.

Definitely call her! Explain she's under no obligation to say yes and you totally understand if she can't do it. More than likely she will be happy to accept - a baby that age can usually be left with someone, and I'm sure she'd be thankful for a night out

Still send her the gift if she says yes if you want to!

I think the bridesmaid proposal boxes are a waste of time and money. They are usually filled with junk no one needs. What could be more personal than talking with someone on the phone or via Skype?

I think the boxes are cute. I'd send them to those who said yes as a thank you for joining me on this adventure.

I'd still send her a box/call and ask! It's an honor to be asked, no matter if she says yes or not.

Side note: Welcome to Texas! I'm from the DFW area.

You could Send a lovely card and hand written note. Include one of your fav E-pics.

I like the idea of Skype-ing with her and tell her something like "hey, you know I love you and would totally loved it if you could be by my side that day, do you think you'll be up to it?", I asked my BM's sort of like this, once I told them the engagement they jumped in to planning mode so it just came out "oh... I'd love it if you could be by my side" and later on I gave them their gifts with a personalized letter saying what they mean to me and why I chose each of them

She could still very likely say yes. I think calling beforehand is fine. Calling all of your hopeful BMs is fine really.

Definitely ask her first, then send the gift - that's what I did with my bridesmaids. Don't assume whether she will or won't want to be part of your day, just ask her kindly and be understanding if she says no. It sounds like you totally would be based on the fact that you're even thinking of this

The boxes of personalized BM proposal gifts can absolutely pressure someone to feel obligated to say yes to being a BM, even when that person may have concerns about finances or their other life commitments.

I would suggest you respect all of the friends you're planning to ask to be BMs by asking them each privately and with no gifts. Extend this courtesy to all of your potential BMs, not just the one. Then you can give them the gifts after they've said yes in a setting where there's no pressure.

Thanks everyone! I just finished video chatting with my pregnant friend and she said yes to being my bridesmaid!

Now on to call the rest of my girl squad - thank you all for your advice!

I wish I could like Muriel's post 10 times.

I would definitely call her first so there isn't any pressure

Oof! that's a tough situation. That is one of those situations you may just need to real talk with her. Talk about the logistics and the likelihood that participating in a wedding, while you would love to have her, is maybe not in her best interest or even possible. especially with such a close timeline.