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Look my best. I like getting ready for a date. Since OLD, I started out my second dating life extremely nervous, and so I've incorporated comfortable clothes I'm able to relax in.
No, I did not put any special effort into looking my best on dates when I was single. I would want to go wearing the things I find comfortable and looking like my everyday self. Mostly because I felt that the more comfortable I was in my attire, the more comfortable I'd be in my skin. The more comfortable I am in my skin, the more easily I can engage in conversation and put my date at ease and we can see if we really connect or not.
My idea of an awesome first date is both of us being able to relax and geek out and be ourselves, really talk and laugh. Not me doing a little spin like a runway model and him buying me an expensive dinner. I want to dazzle a man's mind, not his eyes, and if he's not excited about me the way I generally look, then I would rather pass on dating him. So you bet, I'd show up in my jeans and a GWAR shirt, with no makeup (which I normally don't wear.)
Now if I am well into a relationship, like I am now? Ah, NOW I will doll it up for my man sometimes. I know him well enough to know what kinds of clothes he enjoys seeing on me, and I will dress up nicer to go to brunch with him some weekends at this nice French place we both enjoy. I'll dress nice to be at his side at parties, wanting him to feel like King of the World with a pretty date.
But if I don't know you, I'm not really trying to impress you. But I also add very clearly here, I ALWAYS offered to pay my way on dates. My boyfriend and I (3 years in) still split the check, and I'm 100% happy and comfortable with that. I prefer it. I only let the guy pay if he seems to insist, because I'm not going to make a scene arguing about it.
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