The context of the following conversation is Ash asked dad for some advice on dating, but dad was too embarrassed to reply.:
Ash says I asked my dad about his charming techniques back in the day..
The friend responds Oh, your dad dated around a lot when he was young?.
Ash responds Yeah, I don't think he was very proud. He wouldn't tell me anything..
The friend responds That's strange..
Ash responds I think he was too embarrassed, I'll ask again another time..
The friend responds I'll teach you a thing or two in the meantime..