I guess if $5K isn't shit to you, it's whatever to drop it on anyone who asks, but it's a lot less expensive to just say no 100% of the time. I never get asked for money because no one has ever gotten money from me. Seems like a better move if the goal is to not have people ask you for money. You also mention not wanting to look like a jerk, but I'd rather have someone think I'm a jerk than have them think they got away with stealing from me.