Oh dear. Okay, I’m pretty sure Sherlock despises matchmaking. He’s probably had to suffer it himself in the past. So he’s not so much trying to set Mrs Hudson up with a specific person as…ensure that she encounters potentially compatible individuals in settings where they have sufficient chance to become acquainted.
Let’s say he starts with Angelo. He engineers this by announcing to Mrs Hudson that for all she’s done, he’d like to take her to dinner. And then he drops a word to Angelo that she’s a personal friend of his, so y’know. Give her the royal treatment. And then Sherlock ditches her for the dinner, so that Angelo will spend the evening looking after her.
He’s disappointed when this not only doesn’t work out, but results in Mrs Hudson being more pissed off at him. Also John is taking her side. Bummer. Okay, next target. I dunno who, Sherlock knows half of London. Let’s say they’re a carpenter or electrician or something. Oh, this one’s easy! Sherlock can simply destroy some portion of the house’s infrastructure, sufficient to require the gentleman to spend several days there, fixing it.
When they don’t seem to be hitting it off right away, Sherlock proceeds to lurk around, attempting to make sure that the two of them put their most interesting qualities on display (obvs he wouldn’t pick a lame slouch for Mrs Hudson!). Mrs Hudson ends up flustered, the guy is like, “WTF” and John is like, “STOP HARASSING PEOPLE WHAT IS WRONG WITH YOU.”
So, that’s a no-go. Next one! Only…er, crap, there aren’t many people in London worthy of Mrs Hudson. Sherlock’s going to have to…brrr…utilize Mycroft’s contacts to set up the next one.
There is a long drawn-out scene of Mycroft basically sitting in his chair, staring at Sherlock in disbelief. But Sherlock is like, “FINE I’LL DO YOU A FAVOR,” so Mycroft is finally like, “*snicker* Yeah, okay, sure.”
It’s a total disaster, because it turns out Mrs Hudson knew the guy’s father when she was young and he was a dashing older man working for MI5. Mycroft is like, “BTW THANKS FOR COMPROMISING AN AGENT.” John, who is there when it comes up, is like, “Sherlock. Seriously. What the fuck are you smoking?!” But at least Mrs Hudson had a lovely time reminiscing with the son of a guy she dated, so she’s in a better mood that week.
Sherlock comes up with another batshit idea, but Mycroft is like, “He’s going to ruin Mrs Hudson’s life and get himself evicted, and while John is welcome, I am not putting up my little brother in a spare bedroom.” So he goes to John and explains. John is like, “JESUS CHRIST NO.” He goes to Sherlock and is all, “STOP. I have a plan.” Sherlock, who is batting .000, agrees to give it a shot.
John’s plan is to go to Mrs Hudson and ask her if she would like to go on a date with one of his professors from med school. She thinks that’s very sweet; she always did like dating, and ooooo, a doctor.
“Lovely!” John tells her. “And to apologize for his behavior lately, Sherlock says he’d like to foot the bill for you. So you two go anywhere in London you’d like!”
Peace is restored. Partially because Sherlock retreats to the sofa to sulk for three days.