Dating a Friend from Middle School

Visitor's Question from a 13-15 year old Female
I "dated" this one really great guy when I was it Middle School. Now, years later, he's come back into my life. When we were younger, he was there for me through a really difficult time, so we have a lot of history together.
I was lucky enough to spend some time with him last night, actually, we played pool for like three hours, just shooting and talking. It was so nice to catch up with him, and I found he's just as sweet, and adorable as he was in Middle School. Needless to say any feelings I had for him then have resurfaced, in different forms, but still relatively the same. I really like him, but I'm not the best at putting myself out there, and I don't know how to find out if he's really interested or not. Usually, I date a different type of guy, one that might not respect me, but he shows that he's definitely interested. This guy is so different, but I'm not sure if it's just that he's different and he respects me, or that he's not interested. What can I do to find out if he's interested, or make him more interested? I'd really like to pursue a relationship with him....but sometimes he makes me feel like we're still in Middle School! Help! Advice
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Dating a Friend

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