That’s really nice … I hope that you both will enjoy your date ..

Comfortable and chic ..

I found a couple casual pants outfits.





Remember. He already likes you so no need to try dress like someone else , be you. Wear what feels like you. What makes you feel beautiful and comfortable most of all. You're beautiful as you are and he knows that too.

Olive Garden…for a first date?

I would wear a slight upgrade from what he sees you wear at work

If he doesn’t up his game with the clothes for your date, that’s another red flag (Olive Garden being the first )

Wear whatever's comfortable for you.

Have a good time. ☺️

Olive Garden is casual. Wear something comfy and just be yourself. Have fun.
Good luck and have a nice time together.

Olive Garden is “somewhere nice”? Lol. Have fun, though.

The fashion requirements of Olive Garden and McDonald’s are not significantly different they are both chain restaurants they are both casual dining dress like you go to work. Unless you want to make some kind of impression, then it’s time to think about fashion

Olive Garden is pretty casual. What would you typically wear to work, or a job interview?

Wear what you are comfortable in.
Olive Garden is a very casual restaurant.
You should not be nervous.

Wear something nice like a dress but don't try to over do it, olive garden is casual wear something comfortable but whatever it is don't wear what Queendragonfly suggested that's just a horrible look.

Nope... Don't date co-workers - if it goes bad, you still need to work with them.

I think it just depends on your style and your figure. No need to dress to the nines but make sure that you're comfortable and highlight whatever you believe are your best features to help keep your confidence up. It's all going to be about body language and your comfort levels with each other anyway. Have a great time and he'll have a great time. Fun is contagious.

Asking a co-worker on a date? Big risk in that these days. If he asks someone who's not interested, he could find himself quickly summoned to HR and given a half hour to clear out his desk and head out the door. MeToo has reduced if not flat-out eliminated opportunities for co-workers to pursue romantic endeavors.

Its like eating at the private kitchen of a delightful Italian stereotype

Wear something nice but casual that you are comfortable wearing

It's olive garden .....
Be yourself

Just make sure to shake your money-maker

Olive Garden is pretty casual. Wear something comfortable but nice. Something he hadn't seen you wear to work.

Olive Garden isn’t many levels above McDonald’s.

He's probably keeping things low-pressure. Not my style, but makes sense. I'm concerned about the co-worker angle, though--it can be weird if things go sideways, fyi.

Dress neat and kick back

Olive Garden is more casual than formal, wear something that is comfortable for you.