He doesn't know about the commonly held sensibilities of the people in the 40s. Sure, there's Steve and his preference for old fashioned things that would look better on a grandfather. But there's nothing saying that everyone is like that. Maybe his girlfriend will appreciate the new clothes. If she does, it'll be like two gifts in one.
"Also that you're having fun at this thing, since you're drawing smiley faces instead of frowning ones."
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He doesn't know about the commonly held sensibilities of the people in the 40s. Sure, there's Steve and his preference for old fashioned things that would look better on a grandfather. But there's nothing saying that everyone is like that. Maybe his girlfriend will appreciate the new clothes. If she does, it'll be like two gifts in one.
"Also that you're having fun at this thing, since you're drawing smiley faces instead of frowning ones."