1999
Jax fell for newcomer Chloe, a distant Quartermaine relative and fashion designer. In a scheme to save her company, Chloe entered into a legal (but secretly platonic) marriage with Ned; Jax simultaneously wed Alexis in an equally chaste union in order to lend legitimacy to the Chloe/Ned charade. During the course of their marriages to other people, Jax and Chloe became a full-fledged couple. (V. fell in love with Simon; they got engaged and departed.)

2000
Jax's marriage to Alexis ended, but before he could tie the knot with Chloe, she was blinded in a hit-and-run accident (Helena thought she was running down Alexis). Jax stood by his love, but at the same time, Stefan plotted to use Chloe (who could see through Helena's eyes in her dreams) to monitor his mother. In order to do that, Stefan toyed with Jax's head to make him believe that Brenda was alive. Jax apologized to Chloe, but explained that he needed to find out if Brenda really did survive the car crash. He then left town.

2001
Jax returned with another woman in tow -- Kristina Cassadine, Alexis's surprise younger sister. There was no love connection, however. Jax discovered that ex-lover Angel (who was revealed to be mob boss Sorel's daughter) was in town and connected to Sonny. Jax helped Angel flee after it was discovered that she was the one who had killed her father. Tragically, Chloe was murdered by Stavros. (Her relationship with Jax had been boobytrapped due to a "Dear John" letter that she thought he sent her. Too late did she discover that it was actually forged by Stefan.)