It seems to me that Chrysalis is averse to the concept of friendship due to it’s association with her enemies, but the company of her fellow villains helps her get past that hurdle. She does like them, but can’t bring herself to admit that they’re anything more than co-conspirators. If that’s the case, an enemy mine with her Equestrian foes could be enough to get her past that resistance. She may not understand it at first, but they could help her accept the fondness for them that she once rejected.
Give her some time.
And its worth expanding on for future stories!
Definitely worth a shot. For me, her “socializing” with Tirek and Cozy was time she came closest to became a better person.