The original Chris from OG RE1,Charlie Kraslavsky in the recent interview by Crimson-Head.com confirmed he got directives from Mikami himself telling Jill and Chris have a romantic interest.
That was pointed up also by another serie veteran who worked in RE'96 Jun Takeuchi on 2009.
Resident Evil comics from late 90s feature the pendant Jill's wearing in OG RE1 alternative outfit as a receiver which was given by Albert for undercover STARS operations.
Comics AREN'T canon but I appreciate this detail from STARS days! (I NEED ANYTHING ABOUT THOSE TIMES*0*)
For both OG Resident Evil 1 and REremake Jill's ending with Barry only,he tells about his wife and kids but after saw her sad face,he immediately stops. Then she says it's ok 'cause she knows he's still alive.
Jill's referring to Chris and Barry is already aware of it,that's why he's sorry.
I love the way ValenField's such so damn deep since the very first chapter!