Anonymous wrote:

Anonymous wrote:I'm not sure why people are suggesting you bring a nightgown. Maybe they're 60+?

Unless this was a planned sleepover, you should absolutely not bring something to sleep in. You sleep naked, or you ask him for a soft t-shirt.

Would it surprise or freak you out that there are 60+ year olds who don’t sleep in night gowns or pjs.

DP. Lord some of you are so defensive. You are missing her point. No, I bet it would not freak out the PP to learn that there are 60+ year olds who don’t wear nightgowns or PJs. I bet it would freak her out to find out there are many 25-55 year olds who do.

Anonymous wrote:I'm not sure why people are suggesting you bring a nightgown. Maybe they're 60+?

Unless this was a planned sleepover, you should absolutely not bring something to sleep in. You sleep naked, or you ask him for a soft t-shirt.

Would it surprise or freak you out that there are 60+ year olds who don’t sleep in night gowns or pjs.

Anonymous wrote:Speaking as someone in my 40s, divorced and dating, Im surprised you havent discussed the potential of staying overnight/having sex. The lack of beating around the bush when it comes to…well…beating around the bush, is one of the most refreshing things I find about dating at this age.

That said, bring a small bag, not a huge steamer trunk. Also do bring something cozy to wear when he makes you breakfast the next am. No need to put your clothes back on just to then have them taken off when you thank him for breakfast.

+1

I hope you wore cozy business casual attire!

Anonymous wrote:Ok so what happened? Overly invested in OP’s NYE!!

NP and I agree - I feel like I am in the comments section of Cup of Jo

Ok so what happened? Overly invested in OP’s NYE!!

I hope you had a great night, OP! I’m sure whatever you wore was perfect.

Anonymous wrote:OP- don’t forget to post an update!

+1

OP- don’t forget to post an update!

Anonymous wrote:I'd wear a cute dress. No man is going to be like "oh no, she looks pretty even for an informal sounding night in, what does THAT imply?" No PJs. If you're sleeping over, you won't need them.

And no man is passing just because it involves getting off a pair of jeans.

Speaking as someone in my 40s, divorced and dating, Im surprised you havent discussed the potential of staying overnight/having sex. The lack of beating around the bush when it comes to…well…beating around the bush, is one of the most refreshing things I find about dating at this age.

That said, bring a small bag, not a huge steamer trunk. Also do bring something cozy to wear when he makes you breakfast the next am. No need to put your clothes back on just to then have them taken off when you thank him for breakfast.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:SOS here. I'm excitedly yet newly dating someone for the first time since my divorce. He invited me over NYE to cook a nice meal together with a fancy bottle of wine, fireplace, play cards. I'd assume this includes the potential of sleeping over which hasn't happened yet.

1. What would you wear for a cozy NYE night in?

2. What would you bring to sleep in?

What if your assumption is wrong and you show up with sleeping suit and nigh gown to a dinner invite?

What is a sleeping suit?

OMG I spit out my tea. Definitely pack this as your “sleeping suit” OP and excuse yourself to the powder room around 11:30 pm to change into it. If the night still works out, he’s your guy!

No jeans! Wear a casual dress, something soft or slinky. But not backless and def no sequins.

I'd wear a cute dress. No man is going to be like "oh no, she looks pretty even for an informal sounding night in, what does THAT imply?" No PJs. If you're sleeping over, you won't need them.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:lol by all means show up to his house with a duffel bag full of PJs, toiletries, and change of clothes for the next day. And definitely wear a short slinky cocktail dress for what's being billed as a cozy night in.

(... Seriously, OP, please go with the jeans and cashmere sweater).

Or a nice skirt and sweater.

Skirt and sweater? Some people must be writing from another planet.

Meaning too fancy or not fancy enough?

sounds like a work outfit