I'm going to hang out with a guy I used to date a few years ago. We were never boyfriend/girlfriend, but we dated, had sex, were very affectionate. Now that I have a serious boyfriend, I'm not sure what's the appropriate thing to wear.
-jeans and a cute wifebeater top with ballet sneakers.
I don't know whether to dress up prettily or be super-casual. We're probably going to go to dinner, but probably nothing more than basic sit-down fare. I don't want to look like a slob, but I also don't want to look like a creepy, over-eager ex.
The jeans, because you will look like someone who has moved on and is ok with life. The dress will give the 'I'm trying to make you jealous look'. Also jeans will go with any occasion, the dress might cause issues. And if you don't want to look super-casual were heels.
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