What should I wear on our first date?

It is going to be verrrrryyyyy cold tonight. I don't really have anything super nice to wear but we aren't going anywhere fancy. He told me he's wearing jeans, sneaks and a sweater.

My main problem lies with the shoes lol. I have a nicer pair of dark grey moccasins I was thinking of wearing. I don't really have any nice shoes to wear. I have a pair of black flats but I don't really wanna wear them since it's gonna be freezing. I have a pair of white canvas keds. Then I was going to go with jeans, a casual sweater and my pea coat probably. Ok?

Also, after dinner I was thinking of asking him if he wants to hang out at my house after. Just because we both live at home, my fam will not be home tonight, so it is somewhere to go and hang out. I don't want to go straight home after dinner but I don't want to have to think of us going somewhere and paying to do something, plus by that time it will be about 1030. We are leaving late due to him working. I could suggest we go to my house and watch a movie-- what do you think? I don't want him to get the wrong idea and I don't think he will since he knows me well and knows I won't wanna take him home to get in his pants.


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  • Outfit sounds good with the moccasins. He's keeping it casual so you'll be fine! He may have something else planned for you two after dinner, but if not, suggesting a movie is good.


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