Thanks all.
Astro - I too don't think that he would really think the age difference is a big deal. If I were 18, I would hope that he would. But I'm 25. And an old 25 with a house and job and all the normal things a "grown up" has too. But yeah - I feel like he was kind of feeling the exchange but, when he'd throw something out there, he'd feel stupid and reel it on back in.
If it goes well this next time and I still like him, I think I'll just throw it out there. Just, "Well, if you want to do something outside of work, you know how to find me, and I think we'd have fun" or something.
Elana - I am worried about the "no". But you know... I kind of am starting to think it is worth throwing the danged ball into his court, just 'cause I don't want it anymore!