Holly comes back from Paris after her summer trip with an unexpected piece of luggage, Ben, the British musician she fell for in Europe. Henry and Vince console themselves over losing Holly, but Henry must get his feelings out before heading off to Princeton. Meanwhile, Val gets a proposal from Rick after spending all summer with him.
Holly moves out of the loft and takes up with Ben at the apartment of Gary and a very reluctant Vince when Val refuses to let the two live there together. Meanwhile, Val worries that ending her engagement with Rick was the wrong move, and that her commitment phobia has been a negative influence on Holly.
Holly uses her school book funds to give Ben's music career everything she's got by buying a booking at a music club, but once there, the two find pop star Jesse McCartney also performing. Meanwhile, Rick makes a mistake in asking Lauren to help him buy a ring for Val, as she picks out the one she herself would want instead.
Val tires of Holly's selfishness, after Holly changes her bachelorette party from its original night in order to avoid overlap with Ben's newly acquired gig, and decides to replace her with Lauren as Maid of Honor. Meanwhile, Gary pretends to be a student of dance when he becomes smitten with a friend of Tina's.
Holly enters an Herbal Essences shampoo modeling contest to try and earn money for Val's wedding gift, but after she comes down on Tina for liking her married boss, she finds a spiteful Tina has soon become her contest competition. Meanwhile, Val worries about Rick's preparedness for marriage when she stumbles upon a letter written to him from his former fiancee.
Holly decides that honesty is the best policy with Ben when she fears telling him that she loves him, but hates his new song. She quickly learns that honesty is not his policy when she discovers he's already married. Meanwhile, Val pretends to like all of Rick's hideous bachelor possessions when he starts transferring them to her loft.
While dressed up for a Halloween night out with her friends, Holly conceals the news that she has dropped out of college. Meanwhile, Lauren tries to get Val to unwind from the stress of planning her wedding by taking her to a nudist ranch.
When Holly and Ben begin having a difficult time balancing their professional and personal relationships, Holly enlists Vince s help to set things straight.
Holly asks Vince for help in fixing some problems between her and Ben after their hectic work and personal schedules begin keeping them apart. Meanwhile, Val panics when Rick tells her his parents are coming in on a whim and that they should make their favorite dish, sheep stew.
Holly and Lauren try to keep Val calm by handling all the remaining wedding arrangements, but they are suddenly faced with a crisis when the dress designer dies abruptly. Meanwhile, Holly gets suspicious when she spots Rick with his former fiancee.
As Val's wedding day draws closer, Holly comes clean about Rick's secret rendezvous with his former fiancee, which turns the proceedings into a chaotic mess. Meanwhile, Tina and Vince decide to keep their night together a secret from everyone.
Val s wedding is set to go off without a hitch, but everything takes a turn toward disaster when both Val and Rick get cold feet.
Val realizes that she can't go through with her wedding to Rick, but Holly convinces her that she should still have her Gavin Degraw-performed celebration anyway. Meanwhile, Gary discovers what really happened between Vince and Tina after they spent the night together, while Holly learns that Ben is going on a music tour for a couple of months.
When Val decides she can t go through with the wedding, Holly convinces her to have a personal celebration anyway.
While elated at getting a new job at a music management office, Holly worries that her new boss isn't too fond of her, but soon learns that just the opposite may be true. Meanwhile, Val and the girls go to a ladies night at a club where Val manages to form a bond with another similarly lovelorn woman.
Holly is upset when Ben begins spending most of his time on work, which Vince sees as an opportunity to help his own situation with her. Meanwhile, Val decides to buy a bakery after learning that during her breakup, her business collapsed under Lauren's watch.
When Holly hooks Ben up with a new singer, the attractive vocalist soon gets the hots for Vince, which brings out the jealous side of Holly. Meanwhile, Lauren decides the best way for Val to get a strong critical review upon opening her bakery is to set Val up on a date with the critic himself.
Holly says Vince's name during a kiss with Ben, prompting Ben to break up with her on Valentine's Day. Meanwhile, Gary tells Vince what happened in order to facilitate the match-up of Vince and Holly, but before Vince can rush to be with her, she is given some startling news from Tina.
Holly tries to keep a business relationship with Ben post-breakup, but that changes when he writes a nasty new song about her. Meanwhile, Val's impression of Lauren and Gary's ability to handle responsibility changes when the two inadvertently allow a little girl to loot the bakery.
Val is caught off guard when a handsome plumber (Luke Perry) takes a job at the bakery and she recognizes him as a one-night-stand from her high-school days.
When an attractive plumber comes to the bakery to do some repair work, Val is embarrassed when she realizes the guy is a one-night stand from high school. Meanwhile, Holly keeps Tina on the outs for sleeping with Vince.
Holly invites Gary, Tina, and Ben on a spring break getaway, but intentionally leaves Vince out of the plans as they are still feuding. Vince shows up anyway, and manages to save the day when Holly gets a bad case of food poisoning. Meanwhile, Lauren tries to coax Val into dating a customer, but Val soon learns that the guy is much younger than she thought.
Holly tries to help brokenhearted Ben get over her by setting him up with an attractive vocalist, and rekindles her friendship with Vince when she enlists his help. Meanwhile, after Val gives a homeless man a job, she soon finds herself pitted against Lauren in race to land the guy's attention.
Holly recommends Tina for a job in her office, but is shocked when Tina decides to use sex appeal over substance to move up the ladder. Val chides Lauren for trying to get close to the two handsome sons of a customer who has recently passed away. Meanwhile, the gang becomes a part of Val and Holly's "Gilligan's Island" fantasy during an episode marathon.
Holly has trouble convincing her friends she can cut loose and have a good time, so she concocts a gag which convinces Ben he either has to marry her or face deportation back to England.
Holly's attempt to throw a surprise birthday party for Vince ends badly when he arrives with a date and then confronts Holly about her lack of commitment. Meanwhile, Val meets an attractive single dad, but must dash her own hopes of becoming a familial unit when she realizes she actually likes his young son more than she likes him.
Holly looks to her old boyfriend Henry for advice on why she has trouble committing to relationships. Meanwhile, Lauren manages to get Todd back into the bakery, which provides complications for Val's already-weary love life.
Even though Holly wants to confess her love, Vince gets into a fight with her, because he thinks she hooked up with Henry. Vince then tells her that he's going to spend his summer in Florida. Val gets drunk after learning that her ex is getting married and hooks up with Todd. Holly sneaks into the backseat of Vince's car, but feels stuck when another girl joins him.
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