I don’t think Toby would ever get into a romantic relationship as a proxy, probably not even friends either. Him and Clocky broke up not long after both became killers. Part of it was the fact the two were too different and their morals conflicted too hard; the other was Toby didn’t trust Slenderman enough to be in a relationship. It was a good thing, for Clockwork specifically. Because Toby was right to worry. (More below cut)
Slenderman has a habit of taking away anything that could obstruct his control over his proxies, and that mainly takes the form of people they love.
Slenderman can only reach someone if they’re in a bad enough state of mind; grief, anger, fear, and hate are what he feeds off of, and what he can use to manipulate the proxy into following him. Anyone who can ground the proxy to reality is a massive threat.
Lyra was an example of this. Slenderman was trying to reach Toby for months before he even saw the creature, but was unsuccessful due to Lyra.
That one night when she was driving Toby home, Slenderman was following. On the opposite lane, he could sense another broken mind- one that was very drunk at the moment. The person was just returning from their mother’s funeral, filled with grief and a desperation to make the pain go away. It was the perfect state for Slenderman to take advantage of.
He appeared as a hallucination to the driver right in the middle of the road, able to access their mind through the haze. It sent them into a panic. They swerved wildly and crashed right into Lyra’s car, effectively killing her just as Slenderman had planned.
Similar things happened with other people Toby cared about after he became a proxy. A new friend inexplicably went missing after Toby came over to their house one day. Another fell off a cliff. Several more acquaintances would die or vanish in similar ways, whenever Toby grew too close
Toby knows that anyone he cares about too much will disappear, and he doesn’t want that to happen again. He can’t let anyone else he loves die again. The only person he’s friends with is Kate, and Slenderman only allows this because the success rate of their missions is higher when the two are close.
Toby does still care for Clockwork too. He always has, and he always will, even if it isn’t romantic anymore. It’s more of a nostalgic fondness. And he expresses this fondness through making sure Slenderman never gets to her. Clockwork hates Slenderman, and Toby knows this. He knows how much of a target she’d be. So he’s doing everything in his power to keep her safe from a distance.
girl i sent this email on my birthday apparently?? little snippet of it. it's over 2k words so i'm not posting the whole thing. this is in reference to byatt winsor btw.
"her fear of dying without being signifigant yet also not wanting to stand out and be different is still spinning around in my head... she wants to be remembered and she wants to be known but she doesn't want to be known because she was 'different' or 'weird'. she wants her friends to remember her, but not as the person she is, because she doesn't think the person she is is good enough."