I Love You... Soon
Holly, now working part time at the agency, and Val are excited to meet Val’s acerbic--but very attractive--new boss, Peter, when he arrives for his first day of work. Val struggles to restrain her attraction to Peter. Holly, however, urges Val to date him. But Val soon discovers that Peter is actually a jerk. Meanwhile, after Gary tells Holly that Henry is jealous of her friendship with Vince, Holly reassures Henry. But when Holly inadvertently blurts out "I love you," Henry becomes overly enthusiastic. Holly must explain that she likes him very much but is still struggling with the concept of love. Val is pleased that Holly behaved so maturely but is melancholy that her little sister may not need her guidance as much anymore.
Holly begins to feel stressed from juggling her schoolwork, job and friends--and Henry feels the pain because Holly doesn't support him when he has his wisdom teeth pulled. Meanwhile, after Val becomes frustrated with Peter's business antics and the new male-oriented atmosphere at work, she quits.
When Holly Met Tina
In order to help Val acquire her first client, author Judith Haven, since starting her own public relations firm, Holly reluctantly befriends Judith's troubled teenage daughter, Tina. Meanwhile, Lauren, who is now Val's employee, uses her charisma to distract their former boss Peter when the girls find themselves in direct competition with him for the new account.
Now that Val has quit her job to start her own business, the girls need new office space. With few alternatives, Holly takes the initiative to visit Tina's wealthy former neighbor and convince him to rent the girls his beautiful loft in the city while he serves a jail term.
Like a Virgin (Kinda)
Holly is shocked to learn that Henry has already lost his virginity, and her decision to find out about his former girlfriend leads to some disturbing information. Meanwhile, Lauren devises a plan to get Val to relax and take a day off from work.
No More Mr. Nice Guy
Val confronts Holly about neglecting Henry and spending too much time with cute messenger Vince. Holly reacts by pointing out Val's hypocrisy, and she challenges Val to examine her own feelings for Peter, her handsome former boss.
I'm Sorry, So Sorry
Holly's plans for a skiing weekend with Henry and their friends, including Tina and her boyfriend, Cal, come to a halt when Tina and Cal end their relationship. Holly must decide if she should spend the weekend on the mountain or respect Tina's wishes and not go. Meanwhile, Val's dating advice to Lauren backfires when Lauren's new man, Greg, becomes smitten with Val, leaving Lauren discouraged and heartbroken.
Partially Obstructed View
When Vince arranges for Holly and Tina to go to a band rehearsal, Holly becomes caught in a series of lies. She must make up a story after Henry finds out that she got front-row seats to a concert by his favorite band. Meanwhile, Val goes to a party for the most eligible single men in New York City at which Peter is an honoree, and she is surprised by his attentiveness.
Absence Makes the Heart Grow... Never Mind
Holly thinks she's ready to tell Henry that she loves him, but she hesitates after she considers her lingering feelings for Vince. Meanwhile, Val's first business trip out of New York City is surprising when Peter becomes her neighbor in the hotel.
The Odd Couple
Holly feels conflicted when Henry temporarily moves into Vince's apartment. When it appears that Tina is flirting with Vince, Holly must face her jealousy and figure out what--and who--she wants. Meanwhile, Lauren convinces Val to try a dating service in order to distract her from Peter.
Holly searches the city for Henry after he ends their relationship when he overhears her confessing to Val that she is attracted to Vince. Holly's life becomes even more complicated when Vince find outs about Holly's secret feelings.
The Incredible Shrinking Group
Holly comes close to destroying her friendship with Gary when she manipulates him into arranging a meeting with Henry, who is still upset with her because of her attraction to Vince. Meanwhile, Val convinces Lauren that they should both stop eating sugar, but it's Val's willpower that falters.
After Vince is hit by a car, Holly visits him in the hospital, and they share their first kiss. However, they both realize that they can't date without hurting Henry's feelings. Meanwhile, as they wait to hear about Vince's condition, Val and Lauren vie for the attention of a handsome doctor.
Your Cheatin' Heart
Holly rushes to tell Vince that she saw Henry with another girl--meaning that Holly and Vince can date without feeling guilty--but her excitement turns to anger when she catches Vince in a compromising position. Meanwhile, Gary gets a job at a trendy clothing store, and sales skyrocket when the female customers see him scantily dressed. And Lauren encourages Val to have dinner with a former boyfriend from high school who is moving to New York with his fiancée.
Sky Rink Sucks
Holly and Vince each have different ideas for celebrating Gary's birthday. However, their plans come to an abrupt halt when they discover that Gary's ex-girlfriend Jill is in town and has been lying to him for months.
Lunar Eclipse of the Heart
Holly decides that dating a cute guy--who also happens to be Gary's boss--will be a great opportunity to make Vince jealous. But Gary worries that Holly's scheme may cost him his job. Meanwhile, Val and Lauren's friendship and work partnership are tested when Val contemplates a job offer from a top public relations firm.
Val & Holly's 'Not-Boyfriends'
When Vince's grandfather dies, Holly travels upstate to comfort him--then misinterprets his reaction to her thoughtfulness. Meanwhile, after Val's former boyfriend, Rick, has a near-death experience that gives him a deeper appreciation of life, Val finds him more attractive than ever.
After skipping her admissions interview at Columbia University in order to spend time with Vince, Holly is shocked to learn that the next available interview is not for another year. Val is furious that Holly has once again put Vince ahead of her own future. Meanwhile, Lauren contemplates breaking up with her doctor boyfriend, Brad, due to his uncontrollable giggling during their lovemaking.
The Big Picture
After Henry puts aside his own responsibilities to help Holly with her application for an internship in Paris, she begins to wonder if she made the right decision to end their relationship. Meanwhile, Val meets Rick's fiancée, Julie, who, after seeing former high school sweethearts Val and Rick together, insists that Rick never see Val again.
Rollin' In It
When Holly receives $2,000 from her grandmother for her 18th birthday, she decides to spend it all on a lavish hotel suite. Once again, Val becomes upset with Holly's lack of priorities and vows to teach her a lesson in responsibility. Meanwhile, Lauren's love for money and material possessions causes her fiancé, Brad, to cancel their engagement.
Exasperated with all of the pre-prom fuss, her conflicting feelings towards Vince and Henry and her impending internship in Paris, Holly decides to host a stress-free "anti-prom" at the loft. Meanwhile, Val tries to figure out if the invitation to her ex-boyfriend's wedding that she received is a mistake.
Second Season Finale
Holly is elated to be accepted for an internship in Paris, but when Henry and Vince each kiss her before she leaves, she knows the time has come to decide between them. Meanwhile, in order to distract herself from Rick's upcoming wedding, Val books a trip to Venice with Lauren. However, when Val gets sick and has to cancel, she is pleasantly surprised by a visit from Rick--who is still single. Also, it could become a summer of love for Gary and Tina when they share their second kiss.
Europe Was So Much More Fun
Holly had been torn between Vince and her former boyfriend, Henry. Luckily, her summer internship in Paris came through, allowing Holly to leave both guys--and her confusion--behind for the summer. Holly is excited to be starting college, especially since she and Gary will both be going to New York University. Meanwhile, the public relations business that Val runs with Lauren is still struggling. Holly returns home from Paris with a new boyfriend, Ben, a handsome British rock star. Realizing they've lost Holly, Vince and Henry are heartbroken, and Henry says good-bye to Holly one last time before leaving for Princeton. Also, Val, who has spent the summer with her boyfriend Rick, receives a surprise proposal after she reveals her own surprise.
The Longest Night of the Year
Holly moves out with Ben after Val refuses to let him stay at the loft. When the two end up at Vince and Gary's apartment, Vince agrees to let them stay, in spite of his jealousy of Holly's new boyfriend. Meanwhile, Val is concerned her fear of commitment is affecting Holly and wonders if breaking off her engagement with Rick was the right thing to do.
The Not-So-Simple Life
Holly is so determined to help Ben's music career that she risks their relationship when she uses her schoolbook money to pay for Ben to play at a club where pop star Jesse McCartney is performing. Meanwhile, when Rick asks Lauren to help him shop for a ring for Val, Lauren chooses the perfect ring for herself.
God Help the Mister
Holly reschedules Val's bachelorette party to a different night after Ben gets a gig on the same night as the party. Angered by Holly's actions, Val fires her sister as maid of honor, replacing her with Lauren, who is more than willing to step in. Meanwhile, Gary pretends to be a dance student in order to impress Tina's friend Danielle.
When she can't find a job to earn money to buy Val's wedding gift, Holly enters a contest to become the new "Herbal Essences Girl." A spiteful Tina enters the same contest after Holly criticizes Tina's feelings for her married boss. Meanwhile, Val finds a love letter that Rick has kept from his ex-fiancée and questions whether he is ready for marriage.
Three Little Words
Holly is ready to tell Ben she loves him--until she discovers a secret from his past. Meanwhile, Val and Rick argue over Val's controlling nature, and Rick wonders if she is truly ready to share her living space with him.
Ghost of a Chance
The group gets ready to celebrate Halloween, with Holly and Ben dressed as Sonny & Cher, Gary and Danielle as Ike & Tina Turner, and Vince and Tina as the Simpsons--Homer and Jessica. Meanwhile, Holly holds onto the secret that she's dropped out of college. And, in order to get Val to relax from the stress of wedding plans, Lauren takes her to a dude ranch that turns out to be a nude ranch.
The Gift of the Mutton
Holly and Ben are having a difficult time balancing their professional and personal relationship, so Holly enlists Vince's help with a scheme to solve the dilemma. Meanwhile, Val is given very short notice that Rick's parents are coming for dinner and insists on making his mother's favorite meal--sheep stew.
We'll Miss Gittle a Little
Holly and Lauren try to take care of last-minute details to keep Val calm as her wedding day approaches. However, when the dress designer suddenly dies, the girls must try to salvage Val's dress. Meanwhile, Holly sees Val's groom, Rick, with his ex-fiancée.
The Wedding (1)
Val's wedding day is all in place, including a special musical wedding performance by Gavin DeGraw, but everything takes a surprising turn towards disaster when Holly exposes the truth about Rick's recent rendezvous with his ex-fiancée. Meanwhile, Vince and Tina try to hide the fact that they spent the night together.
The Wedding (2)
When Val decides that she can't go through with the wedding, Holly convinces her to still have a celebration with a personal serenade by rock singer Gavin DeGraw. Meanwhile, Holly and Ben must say good-bye when he leaves for a two-month tour. And Gary uncovers the truth about Vince and Tina's night together.
How to Succeed in Business Without Trying to Be a Lesbian
Holly's excitement about landing a job at a music management firm is cut short when she feels that her new boss doesn't like her. Meanwhile, to help Val forget her troubles, the group takes her to "ladies' night" at a local club where Val bonds with another woman, Michelle, who is also nursing a broken heart, and Holly has a surprising encounter with her new boss.
Don't Kiss the Messenger
When Holly becomes frustrated that her boyfriend, Ben, has chosen work over spending time with her, Vince uses this information to his advantage. Meanwhile, Val learns that while she was dealing with the breakup of her relationship, Lauren ruined their business, prompting Val to unexpectedly buy her favorite bakery.
Sex and the Single Girls
Holly partners Ben with a new singer but becomes jealous when the sexy singer is attracted to Vince. Meanwhile, Val and Lauren get ready to open the bakery, but not before Lauren decides to make sure they get a good review from a local food critic by arranging a date for him with Val.
After Holly calls out Vince's name while kissing Ben, he breaks up with her on Valentine's Day. Meanwhile, Gary plays Cupid by telling Vince about the breakup, sending Vince running to Holly. But it's Tina who hits Holly with the bombshell that will change everything.
Holly tries to find a way to have a professional relationship with Ben now that their personal relationship has ended. However, Holly may regret her decision when he writes a song about what a horrible person she is. Meanwhile at Sugar Babies Bakery, Val has a difficult time trusting Lauren and Gary, especially after she finds out they were robbed by a 10-year-old girl.
Val is caught off guard when a handsome plumber, Todd, comes to work at the bakery, and she recognizes him as a one-night stand from her high school days. Meanwhile, Holly can't forgive Tina and Vince for sleeping together.
Girls Gone Wild
While Holly and Vince continue to fight for their friends' loyalty, Holly purposely leaves Vince behind when she invites Tina, Gary and Ben on a spring break vacation. However, Vince unexpectedly shows up and comes to Holly's aid when she suffers from food poisoning. Back in the city, Lauren encourages Val to accept a date with a handsome customer, Chris, but finds out too late that the date is his prom.
Bad to the Scone
Holly is determined to heal Ben's broken heart by fixing him up with a sexy singer. When she asks Vince for help, their friendship is renewed. Meanwhile, Val gives a job to a homeless man who becomes the object of Val and Lauren's dueling affections.
After recommending to Tina that she get a job where Holly works, Holly confronts Tina when she uses her body, not her brains, to get ahead. Meanwhile, Val argues with Lauren when she uses a customer's death to meet the deceased man's handsome sons. Back at the loft, Holly and Val find solace in a "Gilligan's Island" television marathon--complete with a fantasy sequence featuring Holly as Mary Ann, Val as Mrs. Howell, Gary as the Professor, Vince as the Skipper, Tina as Ginger and Ben as Gilligan.
Pranks a Lot
When her friends accuse Holly of working too much and not having fun, she devises a prank that has Ben believing he is going to be deported back to England unless he marries Holly.
The Kid, the Cake & the Chemistry
Holly plans a romantic surprise party for Vince's birthday. But havoc erupts when he arrives with a date, and Vince tries to get Holly to admit that she can't make a commitment. In the meantime, Val meets a handsome single dad and has high hopes of becoming an instant family--until she realizes the chemistry in the relationship is between herself and the man's 8-year-old son.
My Boyfriend's Back
Holly asks her ex-boyfriend Henry for advice about why she can't make a commitment and the reasons her romantic relationships end in heartache. Meanwhile, Lauren changes Val's love life from depressing to dangerous when she finds a reason for Todd to return to the bakery.
Enough is Enough
In the season finale, Holly is excited to tell Vince she is ready to move forward in their relationship. But Vince, after seeing Holly in the arms of her ex-boyfriend, has had enough and travels to Florida for the summer, forcing Holly to take drastic steps to win back the man she loves. Meanwhile, after seeing her ex-fiancé's wedding announcement, Val gets drunk and wakes up with a ring on her finger--and a surprise in her bed.
I Want My Baby Back
After waking up to find a wedding ring on her finger, Val is surprised to learn that she has married her old boss, Vic, during a wild night in Atlantic City. Meanwhile, Holly is determined to tell Vince that she loves him and hides out in the back of his car as he travels to Florida, but she is heartbroken when she realizes she may have lost him forever.
With Holly and Vince now officially a couple, Holly is determined to make the relationship work even though they must spend a few months apart while he is in Florida. Meanwhile, Val and Lauren devise a plan to force Val's new husband, Vic, to move out of her apartment so they can end their quickie marriage.
Holly and Vince have their first fight when Vince takes Gary to a basketball game instead of her. Holly feels that she and Vince should attend sporting events, plays and other events together, though she quickly realizes this idea may not be for the best. Meanwhile, Vic still refuses to sign the annulment papers, but his persistence may be winning Val over.
I've Got a Secret
Holly is sworn to secrecy when Tina confides that she may have romantic feelings for Gary. Likewise, Vince is sworn to secrecy when Gary confides that he may have feelings for Tina. When Holly tells Tina's secret to Vince, it causes trouble among the friendly foursome. Meanwhile, Vic convinces Val to go on a double date with Lauren and one of his fireman buddies, causing Val to see Vic in a new light.
The Perfect Date
Val tries to convince Vic that their marriage is meaningless by going out on a date with Charlie, a customer in the bakery. Although Charlie quickly becomes obsessed with Val, the date causes Val's feelings for Vic to deepen. Meanwhile, Holly demands that Vince delete the phone numbers of all the girls in his cell phone, resulting in an argument that involves Gary and Tina.
Holly and Vince go to the country for a romantic weekend, and Holly decides she is ready for the next step in their relationship. Upon learning of Holly's desires, Vince feels immense pressure and has second thoughts. Meanwhile, Val is content with spending a quiet night at home, but when she ends up in an interesting situation with Charlie, she calls Vic for support and protection.
Someone's in the Kitchen With Daddy
When Holly and Val's father, Jack, drops in for a visit, the girls do their best to impress him. However, during a nice dinner, Holly and Val accidentally catch their father in a compromising position with his business partner. With all the Tyler family secrets out in the open, the group enjoys a nice evening together.
It's jazz night at the bakery that Val owns, and she finally asks Vic to be her date for the party. Although he initially agrees to the date, things go awry when he shows up with annulment papers. But the signing is delayed when Lauren spills champagne on the documents. Meanwhile, Holly persuades Vince to shave his beard by threatening to not shave her legs.
On Thanksgiving, Holly and Vince discover Lauren kissing Rick, Val's ex-fiancé, and they try to hide the truth from Val. However, the situation leads Val to seek comfort from Vic, and the two decide not to sign their annulment papers.
For Love or Money
Now that Val is truly attracted to her firefighter husband, she eagerly awaits a date they planned. But when she has a big argument with Lauren over Lauren's relationship choices, Val misses the date--and later, she gets a telephone call about a big fire downtown. Meanwhile, Vince feels inadequate because Holly earns more money than he does.
When Vic returns from the hospital following his accident, Val waits on him hand and foot and even gives him sponge baths--leading to some tension due to his physical impairment. Meanwhile, Holly gets jealous when Vince spends time with his new co-worker, and she ends up costing him the job.
Wanting to see Rick, Val's ex-fiancé, again, Lauren stages a phony surprise party for Val. Meanwhile, Vic tries to give Val a special present but can't find the proper time to do it.
The Other Woman
Upon meeting Vic's mother, Eileen, for the first time, Val tries to impress her. Unfortunately, Val unknowingly causes her mother-in-law to take up drinking again. Meanwhile, Holly's jealousy over Vince's new partnership with his co-worker causes Holly and Vince to reevaluate their relationship.
Your Money or Your Wife
Holly and Vince disagree regarding his new working relationship with his female co-worker and decide to spend some time apart. Meanwhile, when Vic receives a clean bill of health from his doctor, he and Val can finally take their relationship to the next level. However, when Val abruptly ends her special offer of free coffee and food for everyone in Vic's firehouse, a rift develops in her and Vic's relationship.
Val panics when she learns that she and Vic were not legally married. Since they must wait 24 hours before they can undergo a civil ceremony, Val and Vic decide to take a compatibility test, resulting in a fight about how many kids each of them wants to have eventually. Meanwhile, Holly is worried that she broke up with Vince too quickly, but after spending time at Vic's family reunion, she realizes she did the right thing.
Friends and Lovers
Val and Vic plan to finally consummate their relationship, but a romantic evening is ruined when Holly, upset about Vince, turns to Val for comfort. In order to get away, Val leaves Lauren in charge of Holly, but the two of them end up behind bars. Meanwhile, Vince accepts a new job in Chicago.
Now and Zen
The day before Val's wedding, Lauren treats her, Holly and Tina to a spa day to celebrate the big event. Meanwhile, upset over Vince's decision to move to Chicago, Holly has yet to learn that Vince has finally realized his co-worker has feelings for him.
Finally. . .
In the season finale, Holly and Val get trapped in a spa, but they commandeer a horse in an attempt to make it to Val's wedding on time. Meanwhile, Gary and Vince say good-bye to each other, as Vince heads to Chicago for a new job. Vic and Val finally tie the knot. Lauren, Gary and Tina all find love. And Holly has a surprise visitor.