Good story so far.

“Only if I can call you “Sweetie”,” he shot back. The all had a good laugh about that,

Should be, They all had

Jack joined in the cheers, even though he felt cold inside; the rum didn’t even effect him all that much;

Should be, didn't even affect him

They ended up in one of town’s less reputable watering holes,

Should be, in one of the town's less


Damn, that's a heartbreaking fic. Poor Jack, alone indeed.

You need to write more, focusing on Jack!