This might be a long one. Assuming that William doesn't die, and Chloe doesn't end up quadriplegic, how does he handle her introducing different people (i.e. Max, Kate, Rachel, Steph, Alex and/or Victoria) as her girlfriend(s)? Obviously he's going to at least be accepting, hence I'm largely wondering how the relationship between him and each possible girlfriend might play out.
Max is by far the easiest, assuming she doesn't move. Max and Chloe aren't sure when they make the shift over from best friends to girlfriends, it's a subtle thing. Their late night games of truth or dare start including little practice kisses that stop being so little or about practice. Their hand holding starts getting more intense. Their cuddling up to watch a movie starts involving a lot more body contact. William watches all of it with a knowing smile and gentle encouragements as both girls come to him, freaked out about their shifting feelings for each other. He probably even brings up the topic of asking Max out on an official date, which freaks Chloe out because 'oh my god I'm crushing on Max, what if I mess this up???' That summer he takes both girls to pride with a 'free hugs from a dad' shirt. It's probably not even the first pride he's been too, I can see him being active helping the community back in his youth because he couldn't stand idly by during the AIDS crisis.
If Max leaves, it's more complicated, but he absolutely encourages Chloe to work up to telling Max her feelings and makes sure that they have plenty of visits together with lots of alone time to work it out.
Kate's an interesting one. Chloe's originally pretty dismissive of her, after all, she's got no use for religion while she's busy throwing herself into science. She's not necessarily an angry atheist type, but she's at the very least agnostic. But Kate's nice to her, she's on a scholarship like Chloe, and she's soft spoken, so all their interactions are positive even if they have nothing to talk about. That all changes when she sees Kate getting bullied. Chloe cannot abide a bully, so she stands up for this girl she barely knows. First she trades blows with her tongue, and then her fists. Chloe wins it, but she's got her fair share of bruises. When William arrives at the office to have a chit chat with Wells and take Chloe home for the day, he finds this mousey little girl sitting outside of the office, wailing about how it's all her fault. He gets the story from her first, and he couldn't be prouder of his daughter. He takes them both out for ice cream, and Kate spends the entire time fussing over Chloe's bruises, which has Chloe grinning like an idiot while blushing and fidgeting from the attention. He encourages Chloe to invite this sweet girl over, but it's not really needed. It's how impossible to miss how blushy they get around each other, and he pretty immediately tells Kate that no matter what, she's got a safe place in their home. Unlike with Max, Chloe's more sure of her sexuality this time around, maybe she's already been to her first pride with her proud poppa, but that cross around Kate's neck still freaks her out a bit, until Kate makes the first move. Maybe it's a stolen kiss behind the bleachers, or she wins a bet over a video game and claims her prize of Chloe's lips, but either way it blindsides Chloe and they fall hard. William tries to help them keep things secret and safe, but Kate's parents eventually learn and when all hell breaks loose, he keeps his word. (Shit, this is a fun premise, I might write this)
William adores Steph from the moment Chloe tells him about her, and he digs out his old DM screen and source books. Steph is amazed that she gets to play such an old edition, and not only that, she doesn't have to run the campaign! It's kind of an open secret between all of them what's going on between them, even if Chloe keeps tripping over herself, and Steph is just as much of a disaster. Instead their player characters start getting romantic toward each other, and William goes out of his way to give them all the setup they could ever want to make it happen. It's not a surprise when Chloe finally tells him that they're dating, but it's still a celebration. He ends up taking Chloe and Steph to pride with Steph's uncle, and they have a gay old time.
Rachel is more difficult. Without Chloe's reputation for skipping class and getting fucked up, she's not going to really take note of her like she did in canon. Sure, Chloe's pretty, clever, and fun, but she's not exactly plugged into the Blackwell social scene or on Rachel's radar. Maybe she pings Rachel's gaydar while she's looking to experiment. Maybe Rachel reaches out for a little extra help with chemistry homework. Or maybe some silly shenanigans happen that put Chloe and Rachel stuck in close proximity, perhaps spin the bottle leading to seven minutes in heaven? However it happens, William is wary of Rachel. He knows her type, and he sees how she's wrapping Chloe around her finger, but he also understands that Chloe needs to make her own choices and mistakes. He's also emotionally available to Rachel in a way that she's not expecting or used to, hoping that he can help her grow as a person and stop trying to wear a mask all the time. Either way he's there for Chloe every step of the way, regardless if it works out or not, and with Chloe having a more solid emotional footing, maybe it goes very differently for both of them.
Victoria is... well he's he's definitely surprised when he walks in on Chloe half dressed and furiously making out with a girl that she's repeatedly complained about at great volume for being a bully. After stammered excuses, a lot of blushing and a generous helping of swearing, both girls get dressed again and William gets to talking with them. He explains that he's not mad, but he's definitely confused, and maybe a little disappointed in Chloe for going down this route, even if he understands it a little bit. Neither girl has a great answer for how this happened at all, a tutoring session that escalated maybe? What really surprises Victoria is that he doesn't kick her out, instead not only does William take the time to ask, he actually listens. She can't believe it at first, but even a few hours with him has her realizing how alike father and daughter are. Eventually Victoria's own dorkiness starts coming out and she starts getting into long debates with Chloe over the merits of this or that anime, they cuddle up and watch classic movies together, she writes poems about Chloe, which is when William starts to really get it. The true game changer is when Victoria's having a really tough time, and not really knowing what to do, she goes to William about it, and he actually listens to her. That gets her bawling, and before long she's blubbering out all the weight of the expectations her parents have heaped onto her slim shoulders. William helps her through that in ways not therapist ever could, and Victoria starts finding the emotional strength to be her own person again, instead of the perfect bitchy princess her parents have been trying to shape her into.
Dana is just fun. He gives Chloe a high five for getting a date with a cheerleader, and her love of Halloween and classic movies means she fits right in with the Prices to the point Joyce rolls her eyes and makes a comment about 'there's three of you now'. William absolutely digs out photos of Chloe's old costumes to show Dana, much to Chloe's embarrassment, but her protests die away as Dana squeals about how cute she was. They end up doing an ensemble costume for every Halloween until Chloe and Dana are off at college.
Alex is going to be something that happens later in life. Chloe's been off on her own for a while, been through college, maybe even has her masters. Chloe stays in touch with her dad pretty regularly, at least weekly phone/video calls and visits for the holidays and she comes to him for advice on a lot of topics. He first hears about Alex on one of these calls, maybe she's a mysterious stranger that Chloe is helping out, or a traveling musician that she's hit it off with. Then come the pictures, and oh wow she's cute! Chloe's all blushes and excited babbling about her, how funny and smart she is, and links to her soundcloud while raving about her music. Chloe tries to coax Alex onto a call, but she's really shy about meeting anyone when she can't see their aura. Finally the holidays arrive, and he meets Alex, who is a giant bundle of nerves in a denim jacket. William is his usual gentle, gregarious self and Alex wonders how she was ever surprised that William is as genuine as his daughter. It doesn't take long for William to start becoming a father figure in her life, even if the -in-law bit might take a long while. That title is very much a formality as he takes her, and Gabe, under his wing, being every bit the father that John failed to be. She honestly has a few good, long cries over it. He also spoils the shit out of Ethan and gets stoned with Char, so that's fun.
If Chloe ever brings Cassidy home, he makes her take a fucking shower and then pulls out his own guitar.
