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Hey Ladies, some advice please(kinda long)

post #1 of 5
Thread Starter 
So Im newly single and totally ready to mingle I felt trapped in my relationship for a long time, so im totally ready to date and have some fun!

But I need some advice, so heres the history. My family is very good family friends with this other family that owns a jewlery store. The son and I actually went to the same highschool,though we didnt know eachother then cause we were in differnt grades, hes older by 4 or 5 years. I've always had a little crush on the son, but I've always been in a relationship, or he has, not to mention he is a family friend so I didnt want things to be weird. So I had totally forgotten about my little crush until today, I went shoping with my mom, we went to the jewlery store and the son was there. I was sitting there talking to his mom and one of his co workers about the relationship I just got out of, and I was telling them how I wasnt happy, I felt stuck, and I couldnt picture myself marrying him, so I broke up with him before this relationship got any longer, I didnt want to be with someone cause i was "comfortable." So we were all just chatting and I swear he seemed differnt towards me sort of, like more into talking to me then he usually is,smiling,asking me questions and what not. My mom and I left in her car to the mall, and we left my car at the store.
In the car my moms telling me how perfect me and the son would be for eachother, how we have everything in common yadda yadda yadda. I agreed and told her I wasnt agianst the idea of going out with him, I just get so shy around him(and im not normally shy!). So we get back to my car and my mom drops me off, she leaves and I go in the store to let them know im back. Thats when I realized my mom had my car keys, I called her but she wasnt answering her phone, I finally got a hold of her after she got home, I told her I needed her to come back, she told me to have the son drive me up, i felt weird, so i told her to just come get me, she said ok and we hung up. 5 minutes later the son comes out with his bag and tells me he is driving me to get the keys(thanks mom!lol), so he takes me in his car and we small talk, i swear it seemed like he was interested but im dumb with interpiting signs and such. Earlier in the day when i first came in he had told me about this Halloween party where you can bring your dogs, he said he would get the info and let me know. So when i was getting out of the car I said, hey let me know about the halloween party with the dogs, he said he would call me and checked to make sure he had my number (we never talk on the phone or hangout before, we just see eachother at the store) So he said he would call me, so lets see if he does. When we were in the car he was asking me about my ex and the break up, I was telling him how I need to start going out and doing stuff, that I've been cooped up for a year and havnt done anything, im going stir crazy. I was hoping to drop a hint like I want to go out or something, but im bad at that too.

The reason I need advice is cause this isnt just a random guy I've met, he is a family friend, so I want to make sure he is interested before I flirt to much or ask him out, I dont want it being akward, ya know?

So how do I go about this? If he calls me to tell me about the halloween party, should I ask him if he wants to go see a movie? What should I do and what do I say? I hate approaching guys, I would rather be asked out, but I have learned you cant wait around forever, sometimes if you want to get things done you need to do it yourself, plus a lot of guys are intimidated by women and wont aproach them. But I think this case is a little unusal, since we are family friends, he could just be nice to me cause we are family friends.
The thing that kills me is that we would be so perferct for eachother, we have everything in common,our familys are super good friends, and he LOVESSSS animals, he doesnt travel anymore cause he doesnt want to leave them, I do the same thing!lol

So ladies, what would you do if you were in my shoes?

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post #2 of 5
My advice is to treat him like you would any friend, male or female, then see if anything develops out of that.

Cheers, from
post #3 of 5
Yes, I would try to start hanging out as friends..don't make it sound like a date, but that you should just hang out sometime.. Then if you really are perfect for eachother, more will develop..

If there is anything I have learned..lol..it is DO NOT RUSH anything. But ease into it, and make little subtle gestures here and there that you are interested.

Goodluck!! I know how you feel
post #4 of 5
Thread Starter 
Ok so how do I become his friend without seeming like im interested, since we have never hung out before or talk on the phone?lol, im such a dork.
post #5 of 5
Originally Posted by Sydney View Post
Ok so how do I become his friend without seeming like im interested, since we have never hung out before or talk on the phone?lol, im such a dork.
Just say casually..."do you wanna grab a coffee sometime?" or "we should go for lunch"..

If he is remotely interested, he will say yes..and they are casual type "dates" so it doesn't seem datish...does that make sense?
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