How do you pursue deep friendships? How do I tell someone I really appreciate them?

I'm friendly, a goof, and have had many friends, but in terms of having a really good friend to talk to, I can't name anyone in my life who has played that roll. It might be because I'm shy, scared of embarrassing myself, or scared of trying and being hurt. I know is that I'm tired of playing relationships safe, because the more shallow they seem, the more lonely I feel. This reflection has made me realize I don't really know how to make close friends. I've tried just being myself, but I tend to coast and not be very intentional.

I started interning with another guy two months ago. We have a lot in common (same major, beliefs, movie tastes, personalities, etc.) , have hung out a quite bit and pranked the office together. We get along pretty well. I'm think they're super fun to be around, and he is totally someone I could see myself being really good friends with in the future. However, I am a poor conversationalist, and don’t know if he also want sot be friends or he’s just being polite.

We both work at a university, and are going back to School in September. We might see each other around, but I fear that when we get really busy, and stop hanging out. As a result, I feel like I should take a risk to try and deepen the friendship or see if he even wants to be good friends. I’ve thought of just telling him how I feel about it, but is it weird just to tell a friend how much you appreciate them? How would you do that? Should I think of something else?

-An Awko Taco