This might be more a hot take than a confessional. I think PCs pursuing a romance with Strahd is boring 90% of the time, but Strahd pursuing a romance with PCs is funny 100% of the time. He's horrible and evil and manipulative and he's also sooooooo old and embarassing. He'd take you on dates to Golden Corral and ask for a senior discount while telling them you're a child under 12 so you eat free.
THIS IS CORRECT. THIS TAKE ISN'T HOT AT ALL IT'S JUST CORRECT. THIS IS HOW MY STRAHD ACTS WITH VANYA TOO
"my treasure, please do not forget to wear the Special Outfit I had fitted for you" [the outfit in question is overalls and a propeller hat]
The way Luz's thank you drawing got rejected by the person it was for when she thought she finally found someone who wouldn't make fun of her for her eccentric behavior, that she is worthless..and then the drawing does get recognized, that it's beautiful and why would it get thrown away. She was finally understood (I am in shambles help-)