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I asked my best friend out for Valentine's Day.
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My best friend and I have known each other for close to a year now, I've had feelings for her since October of 2023 but she had a boyfriend. They broke up a few months ago and I didn't want to tell her as I wanted to respect her and I will be leaving for the Army soon. We have been hanging out increasingly over the past few months and more and more people have caught on to my feelings toward her including her mom. We always hang out after our college courses and while I was driving her back to her car I decided to ask her. Mind you I was terrified as I value our friendship but, I tried to get the words out then gave up and drank my Starbucks, she asked if I wanted to say it again and I told her to forget it. I thought to myself "If I don't do this then I will always be a scared little boy" so I looked at her and asked "Could I take you out for dinner tomorrow night (February 14th). She kinda got quiet and a text came through the phone she looked at it for a minute then asked "What kind of dinner is it" (I now think she was asking if its a date but idk) "What if the restaurants are full", I said "Whever you want to go" "Dont worry Ill get us in anywhere". She joked "We can't break in" I playfully punched her and told her I dont have to do that. I apologized for asking and she said not to as she liked and appreciated that I asked her. She then apologized as the text was from her mom, her grandfather wasn't doing any better and she explained she was worried about the five assignments due on Thursday. I told her "Listen, if you don't want to, or you can't make it, it's ok, I'm not going to hate you or treat you differently, you're still my best friend". She wasn't too worried about getting off late from work, mostly school and her grandfather. When we got to her car I helped her with her things and we hugged each other, she said she wou,d let me know, and we left. We always get food together but I've never asked her out like this. I've wanted to ask her for a while which she knows, but I'm scared of losing her as a friend, we normally can read each other like a book. I know it's a long post but I'm having second thoughts now and I figured I'd just ask.

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9 months ago