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Technically for a first date...

4 replies

OnceMoreIntoTheBreachDearFriends · 19/01/2026 17:32

Bit speculative as based on my other thread I don't even know if I'll be going ahead with this... reconnected with someone from school recently (so someone who's known me since the late 90s and has seen me in all manner of 'fashions' and also my granny pyjamas along the way). I've insisted if he wants us to make it work as a couple I want to do things properly in terms of meeting for actual dates

Stupidly (since I have ASD and am usually anal about planning things) I've told him to surprise me tomorrow night and take me somewhere...but he's giving me no clues about where. It won't be anywhere super glamorous since it's a Tuesday night in a small northern town, but I have ZERO IDEA what to wear to cover all eventualities.

I'm 5'1" since 6 but with curves. I have pretty much a bit of everything in my wardrobe... I just can't choose something!

OP posts:
ThatCraftySquid · 19/01/2026 17:36

Smart trousers, trainers and a top (even a tshirt) with a blazer? and if it's your style, a funky necklace? Should cover pretty much everything.

Or if you are comfortable, a midi or maxi dress with a tshirt and blazer, or a big jumper if you like and are happy with casual.

What I would do is plan outfit , and then send him a message: planning to wear this, will I be warm enough of do I need more layers? If he's planning an outdoor activity in the rain, he should tell you!

Shemadewaffles · 19/01/2026 19:34

You don’t know whether you’ll be going ahead with a date for tomorrow night that you’ve said yes to?

Shemadewaffles · 19/01/2026 19:39

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OnceMoreIntoTheBreachDearFriends · 19/01/2026 19:40

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Yes he does - not that that has any place on a thread where I'm asking for advice about an outfit

#where'sthefuckingeyerollemoji

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