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First date look (omg)

10 replies

ChicJoker · 16/01/2026 18:29

So I have a first date coming up. For the first time in absolutely forever (I feel sick!)

we’re going to a very nice restaurant (my choice) and then out for drinks. The person I’m dating is extremely well off and went to boarding school and finishing school/etiquette lessons - first of all, in case I’m missing anything with this any tips are welcome. Generally my etiquette is very good, and they are very much “into me” and are coming off as quite grateful to be in with a chance sort of thing.

what do I wear??? My style is usually quite trendy but sexy, I am a “dress up” kind of person and would say my day-to-day style is on the dressier side. I avoid pattern.

i am 5’5. My measurements are 34 27 38 last time I checked. I don’t LOVE my legs but for the right dress wouldn’t mind. My arms aren’t my favourite feature. My chest back and middle are probably my best features.

i don’t know why I’m panicking so much maybe it’s because I haven’t dated in so long but honestly im so uninspired!

will be booking hair and makeup on the day too so feel free to style along with this in mind.

TIA!

OP posts:
fedsup · 16/01/2026 18:32

What do you feel more comfortable in? dress, skirt, trousers?

ChicJoker · 16/01/2026 18:34

fedsup · 16/01/2026 18:32

What do you feel more comfortable in? dress, skirt, trousers?

I think dresses! But I’m venturing more into skirts/trousers/tops now.

forgot to add my colouring! Very dark brown hair about waist length, brown eyes, medium skin tone. On colour analysis apparently im autumn but one did say winter 😂

OP posts:
fedsup · 16/01/2026 18:49

And what do you have in your wardrobe that you feel comfortable in for going out in?

ChicJoker · 16/01/2026 18:51

fedsup · 16/01/2026 18:49

And what do you have in your wardrobe that you feel comfortable in for going out in?

I’ll order something new!

OP posts:
fedsup · 16/01/2026 18:55

Sorry I meant as a guide or do you want something complete differently to anything in your wardrobe?

Sodthesystem · 16/01/2026 19:26

If it's just a first date then don't overdo it. Dress venue appropriate.

If the hair, nails, make up etc is for you, to make you feel more confident then great! So long ad you aren't putting yourself out financially too much. But don't do it just to impress him.

It's date one. By date 3 or 4 you can make more effort if he's still about.

Plenty of more affluent and educated men can still be rubbish.

A shit in a box is still a shit in the box no matter how shiny the wrapping paper.

To be honest usually the most fun part of the date is shoping for new clothes before it xD

But good luck amd have fun!

dammit88 · 16/01/2026 19:28

How old are you?

Ialwaysthoughtitwasadojo · 16/01/2026 19:31

If you show us some outfits we can advise! Trying to just picture it off the descriptions given is quite hard.

TheLOUDNESS · 16/01/2026 23:44

Men don’t attend ‘finishing school’, @Sodthesystem - so I wouldn’t assume the OP’s date is male. But whatever, it sounds as if they already know each other, so it’s a bit more of an event than a first OLD half hour in a coffee shop.

I slightly feel it’s a shame you’re not going for drinks first, and then dinner.

Perhaps if you suggest a budget it would be easier to imagine what sort of look you’re aiming for, @ChicJoker.

TheLOUDNESS · 16/01/2026 23:46

(But why would anyone who went to any decent boarding school require subsequent lessons in etiquette?)

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