sounds like a work outfit |
| 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. |
| No jeans! Wear a casual dress, something soft or slinky. But not backless and def no sequins. |
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! |
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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. |
And no man is passing just because it involves getting off a pair of jeans. |
| OP- don’t forget to post an update! |
+1 |
| I hope you had a great night, OP! I’m sure whatever you wore was perfect. |
| 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
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| I hope you wore cozy business casual attire! |
+1 |
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. |