What’s the best way to respond?

Guy I’ve been talking to/seeing for 3 months is on the smaller side down below. It doesn’t bother me cause he knows how to use it, but he makes comments about it sometimes or sends meme type videos and I never know how to respond🙃
Im awkward and never know if I should go along with the humor or tell him I like it (I’ve obviously implied that)
What response is best?
What would you want to hear?
What’s the best way to respond?
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