I asked HIM (my close friend) out, so should I pay? And how can I pay without making him feel emasculated?

Anonymous

Background: Hello! ^___^ So I finally worked up the courage to ask out one of my best friends a couple days ago. He said YES! We're both seniors now, and I've liked him since 8th grade; allegedly he always thought about what'd it'd be like if we were together since freshman year of HS. We went to the same middle school, but we don't go to the same high school. We always hang out outside of school. Since 8th grade he's come over to my house for summer, Halloween, Christmas, and friend hangouts. He was also my escort when I won homecoming Queen runner up. We've done a few "date-like/ one-on-one" activities with each other like volunteering, or seeing the Pixar orchestra together, but we've never had to deal with paying for things. The food just happens to be free. However when we've done afternoon volunteer work, he's offered to get me something to eat snack and drink wise, I just say that I'm fine.

Question: I asked my close friend on a movie date. He has a job, and he's not a typical alpha male but he does like to be a gentlemen. Since I asked him out, I think it's right for me to to buy his ticket. Right? XD I don't want to "emasculate" him trying to buy his ticket for him. Should I just purchase them online or before hand & say, "You can get them next time ;-) "? If he insists, should I let him pay for popcorn or something? I want to go to Dave N Busters after to eat. Should we go dutch/should I let him pay? I'm just really confused, being that I heard that on a first date the ASKER should pay. But I feel like if I pay for everything (He'll def offer to pay) he might not feel manly & loose interest ;---; He has a job (I don't) I feel like he wants to be chivalrous. We'll always be best friends but he might not want to go on a 2nd date if I make him feel "worthless". If the roles were reversed & he asked me out, I feel like he'd want to & would be expected to pay for most of the date. Should I just do what a guy would do & pay, even though he's the confident type?
I asked HIM (my close friend) out, so should I pay? And how can I pay without making him feel emasculated?
I asked HIM (my close friend) out, so should I pay? And how can I pay without making him feel emasculated?
Updates:
+1 y
Thanks so much for all the quick responses you guys rock!
+1 y
I'll definitely pay for the tickets
I asked HIM (my close friend) out, so should I pay? And how can I pay without making him feel emasculated?
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