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what do i do now? need advice!!

I need to provide backstory in order for this story to make sense. I am a 20 y/o female, and this guy i'm talking to is my age. We met in elementary school, where we were good friends and stayed that way until he moved away. Mind you, we haven't seen each other face to face in nearly 10 years, and have just recently come into contact with each other via social media. I was the one to follow his account, but he was the first to intiate any conversation. So, we talked some during the summer, but then he went to military boot camp and the conversation fell off. What I'm wondering is multiple things: should i keep contacting him, since i am always the first one to text; could it be weird for him for me to keep messaging him? Secondly, the conversation he originally began with wasn't just "hey, how are you?", like he asked me about my life and is it weird that I find that attractive? The thing is we haven't seen each other in years, so I probably mean nothing to him. But i keep getting this feeling that i should keep trying to maintain contact? Any advice?
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Contact him. Tell him you understand he can,'t contact you until family day when he gets his phone back, but see if you two can visit after he finishes AIT. And by getting together, I mean he spends his pay to get a hotel near you, staying in a hotel near you. Yes, this implies intimacy, if that hasn't happened before.

Also, if he is a basic infantryman, a little loophole most are not aware of until it is too late. He can arrive to any US Army installation that has infantry and say upon showing up (act like a dumbass) if this is where he is supposed to go, if his unit is there. Army doesn't care about a guy fresh out of basic training, he has no record and can fill any infantry role (except airborne or special forces, don't try that). They will call him a idiot, smack him up the head and make him do a bunch of push ups, but will also enroll him at that base. You can't do that later one, because they give you new orders based off your record.

I would recommend snatching him up for a relationship now as you already know him well. You can marry while in college and he can be what is called a geographical bachelor because you live apart. It will effect any low income grants you receive if married to him.