Time of Your Life - Season 1 (1999)

Having money problems, Sarah and Romy throw a singles party for profit in their apartment. During the party, after getting a letter from Bailey in San Francisco announcing their breakup, Sarah decides to do "something outrageous," with her now free-spirited life which leads her to drink, party, get a tattoo and consider spending the night with Spencer. Romy also becomes concerned about J.B. who becomes acquainted with a few too many girls that show up. Meanwhile, Maguire gets jealous when a musician friend of his, named Kenny, hits on Joss. Also, Cecilia becomes ...

Sarah is steered toward a singing career by a "well-connected" man, named Tony. But Maguire correctly suspects that Tony is interested in more than Sarah's music which she asks a reluctant Maguire to pose as her boyfriend to Tony. Meanwhile, J.B. is unavailable to celebrate Romy's success when she lands a small roll on a TV soap opera when he renews a secret relationship with Joan, a wealthy older woman whom he relies on for his income and personal pleasure.

After hitting a snag in her recording plans when Tony's shady business partner is arrested for income tax evasion, Sarah find herself hosting a Thanksgiving dinner with a quartet of suitors who include Maguire, who resents spending the holiday with anyone, the caterer Spencer, Tony, and a schizophrenic homeless man named Jerry, who turns out to be a former opera conductor.

Sarah learns a dark part of Maguire's drug addicted past after the arrival of Taylor, an old friend of Maguire's who spent 18 months in prison for drug possession, which ruins their first date together. When Sarah decides to break up with Maguire, her decision changes when he proclaims his love for her. Meanwhile, Romy presses the issue of J.B.'s lack of intimacy with her and begins to think that he does not like her, while at the same time, J.B. continues his involvement with Joan and is torn between both women since Romy wants his love, and Joan just wants ...

Seeking another better paying job for the Christmas holiday, Sarah gets a big break when she goes to work at New York's Bloomingdale's and gets a lot of commission for a personal shopper. Meanwhile, Joss' problematic sister, Casey, pays a visit and reveals her pregnancy. When Joss and Casey travel to Queens to visit their parents, their mother does not hide her contempt for either's lifestyle. Cecilia gets pneumonia, but refuses to seek treatment until she collapses where Sarah finds her, takes her to a hospital, and learns that Cecilia uses someone else's health ...

As New Year's Eve towards the new millennium approaches, bad luck happens to everyone starting when Maguire's apartment is robbed and he takes it out on Joss, who gets fired from her job at the bar and she takes it out on Sarah and Maguire, in which Sarah learns of Joss and Maguire's living "arrangement" after a grumpy Romy kicks her out of her apartment and takes out her anger on everyone over J.B. two-timing infidelity. Meanwhile, J.B. stumbles into a dream date, named Angela, for the event approaching. Maguire then looks up Jessica, his old girlfriend, to find a ...

Sarah, Romy, and Joss get together and decide to form a contest to see who can have the first meaningful dating experience for the new year, which leads to all three of them to a series of men with varieties of baggage. Joss tries dating a man at an AA meeting, then meets Frank, a single parent with an eight-year-old daughter. After a failed attempt with a guy in an acting class, Romy meets a newspaper critic offering her a chance to succeed in show business with a good review. Also, Sarah meets an unbalanced artist, a closeted voyeur, and eventually an angry Spencer ...

In the days before Sarah's 21st birthday, the word "difficult" defines Sarah's new charge as an au pair to Ashley, and her rebellious teenage daughter Flynn, as well as dealing with Spence himself, who's still angry at Sarah since their failed time out, as well as his new girlfriend, a not-so-bright model named Leya. Meanwhile, Andy Beam, the smitten orthodontist whom Cecilia met during the Sarah and Romy's party months earlier, hires her as his new receptionist where she's liked by him, but not the patients. Also, Maguire and J.B. decide to go into the party-DJ ...

In the month since she turned 21, Sarah is still working for Ashley at being her Lamaze coach, and dealing with Spencer who's still having problems with the beautiful but dim-witted Leya. When Leya leaves town for a photo shoot, Sarah attempts to fix up the continuing feud between Leya and Spencer by sending him e-mail messages which soon lands Sarah in a bind which she must keep of the charade of playing Leya over the Internet for a clueless Spencer. Meanwhile, Romy is taking acting classes to expand her acting talents when an old best friend, Molly, a talkative and ...

Molly jumps in when Romy can't join Sarah to audition for a jingle-singing gig, which they win together. But later, tragedy precludes them from doing the job when Molly is killed by a mugger in a deserted alley. This devastates everyone, especially Romy, who feels frustrated at not being able to have done anything for Molly. After an encounter with Molly's visiting father, Romy decides she needs a break from the city. Maguire also deals with his own anger and frustration and gets no help from Joss, who does not think that it's a big issue. Also, Sarah deals with her ...

In the days after Molly's murder, Maguire fortifies the apartment for a tense Sarah still in fear for her own safety, while Spencer offers her a distraction by taking her out to a dance club, which reinforces Maguire's jealousy. Meanwhile, J.B travels to Portland, Maine to ask Romy to return to New York where he also squares off against her father when she doesn't want to return with J.B. to the city. Also, Cecilia and Andy's relationship grows to a point of intimacy where he finds the sex with her an adventure, but she mistakenly thinks that's all he's interested in.

Spencer discovers Sarah's role in his e-mails with Leya while she is reluctant to start dating him again. Meanwhile, Romy fires her agent in a frantic career drive that prompts Sarah to set her own sights once again on her singing career and asks Maguire for help. Romy tries to get into an off-Broadway show, but learns that she cannot get in without an agent, she resorts to lying and cheating her way in and becomes the lead actress' understudy.

Sarah, more discouraged then ever on what she wants to do with her life, gets an idea when she helps Spencer out with a web site launch party and decides to open up her own temp agency. But when Sarah manages to finagle her way into a high-powered company to land her first client, Spencer is less encouraging after his own web site fails. Meanwhile, Romy and Aaron, the assistant director for the play she is understudying, spend time rehearsing together which makes J.B. jealous.

In an attempt to impress her first client, Sarah turns the record/CD store into an office for her new business, called "Temporary Sanity," with a little help from Maguire and Spencer. But when Maguire's boss discovers him assisting with another business in the store, he fires him and Sarah feels guilty. Meanwhile, Romy sees that she needs to make some changes in her own life with J.B. when Aaron tells her that he happens to be HIV positive which puts a new view in Romy's head on life in general. Danny, Joss' new wealthy investor boyfriend, tells her that he's going to...

With Sarah's temp business really taking off, she asks Romy and Cecilia to look for more temp employees. When Spencer hires a consultant to meet with Sarah, without her prior consent, she gets angry at him about him trying to run her life, as well as arguing about their sex life, or lack of it. Meanwhile, J.B. teams with Danny in his stock investments with making money and soon brings in a lot with J.B. hoping to make enough money for him to move away from New York. But later, J.B. thinks that the whole thing could be a scheme that Danny is trying to pull over when a ...

After Sarah finally breaks up with Spencer after telling him that that their relationship cannot work out, he withdraws all of his investments into her agency, which takes a turn for the worse when a disgruntled client sues her. Meanwhile, J.B. is trying to land a new client for his sales scam and finds one, only that the client turns out to be an undercover cop who arrests him for insider trading and mail fraud in which after questioning J.B., begins investigating Sarah. Also, Romy continues to audition for a Broadway role, and Cecelia's relationship with Andy grows ...

After Detective Gordon Merrin reveals to Sarah that he is her biological father, she is a little disappointed that Gordon is just an ordinary person who has been married and divorced three times, and has nothing but contempt for her mother who abandoned him over 20 years ago. Meanwhile, J.B.'s trial for his involvement in the money scam begins in which he gets a three-month prison term and is forced to say goodbye to Romy, who finally goes on her way after she lands an important role in a major Broadway play. Joss decides to revamp her own career by landing a ...