I don't personally ship ticciwork, but their creators have literally said that they're dating, so I had to.

Slenderman - "No."
Sally - "Eww! Boys have cooties!"
Laughing Jack - "Nope. I know I don't really age, but because I've been around since the 1800's, it seems like everyone's too young for me!"
Eyeless Jack - "Everyone here is either taken, female, or human. But I'd really like to find a nice demon guy to settle down with some day."
Ben Drowned - "Everyone here is too old for me. Except maybe Nina. But I wouldn't date her even if my afterlife depended on it!"
Jeff the Killer - "Kate. She's almost as beautiful as me! Almost."
Nina the Killer - "Jeff, duh!"
Homicidal Liu - "Me and Sully never seem to like the same girls, so dating is really hard. We've pretty much given up at this point!"
Clockwork - "I've been dating Toby for years."
Masky - "I'm not interested in dating. It gets in the way of my job as a proxy."
Hoodie - "D-Dating!? Me? No, I - I haven't thought much about it! I- I'm too busy! Yeah, that's it! B-Busy!"
Ticci Toby - "I-I'm already in a r-relationship! With Clockwork. I- I thought e-everyone knew that!"
Kate the Chaser - "I like Jeff. He's actually pretty cool, and we wear the same outfit!"
Nurse Ann - "I'm far too busy for love. Do you have any idea how often these guys hurt themselves!? It's more than you'd think."
Judge Angels - "I like Bloody Painter!"
Bloody Painter - "I like Judge Angels. She's cute."
Puppeteer - "Zero."
Zero - "Puppeteer."
Kagekao - "I already date Sadie."
Suicide Sadie - "I'm with Kagekao."