Reply To: How To Approach A Boy I’ve Had A Crush On For Months

Typically teenage boys don’t understand subtlety.

I know that putting yourself out there is scary, but my recommendation is to simply compliment him. You’re watching his every move as it is, so I expect you’ll notice if he handles a situation well or does something impressive. So if he handles a spat at DnD – afterwards, or within a day or so – say “Hey, you handled that really well. I think the group appreciates how you manage the club.” or something more teen-speak but you get my point. Drama club – “I think you could totally be Sky Masterson (or whatever leading role).”

If he wants to continue the convo – he’ll make time. Everyone loves talking about themselves. If he’s not interested, he’ll agree with you that he’s awesome and he’ll figure out how to bow out politely (“Thanks, gotta run.”)
Or he’ll be a dick and then you’ll know that he’s a dick.