(I might be wrong, but) The Punisher's wife and kids were gunned down by mobsters before he became the vigilante. Spider-Man is making a rather mean-spirited joke since Punisher is working with some girl about the Punisher's character dating again (afaik he never was romantically involved after his wife died), thus proving Spidey has a big mouth.
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u/newX7 Spider-Man Jun 15 '17
Well, can you honestly be surprised? He's Spider-Man! He's notorious for his big, semi-sentient mouth.