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There are a dozen reasons why making Gilfoyle his best man is a dumb idea. He constantly makes his disdain for the institution of marriage known, as well as his derision for Dinesh and Kelsey for participating in such ‘traditionalist Judeo-Christian bullshit.’ He doesn't ever help Dinesh make decisions on the wedding planning; the date and venue are met with a “Sure, whatever,” and Dinesh’s very carefully crafted Pinterest board of mens' tuxes gets a snort and a “definitely that one” that Dinesh is pretty sure is sarcastic. It's about what he expected from him.
It's even worse because Kelsey fucking hates Gilfoyle. She's started trying to suggest that maybe Dinesh should consider switching and making fucking Jared his best man instead. That would probably be a good idea if they wanted to make the wedding run more smoothly, because Jared is an absolute beast at organization for stuff like this, but Dinesh will never actually do it, because Jared is super lame. Besides, despite everything he always says to the contrary, Gilfoyle really is his best friend.
More than anything else, though, making Gilfoyle his best man is a monumentally, disastrously stupid idea because Dinesh is still in love with him.