About the Show

Season Two started off with a big surprise—Bobby was the guy PJ chose to take to Italy. Even Stephanie didn’t see that one coming. Back in Chicago, Brendan was freaking out about the changes at the radio station while Mike was busy hooking up with a Crowley’s bartender. Unfortunately, his late night rendez-vous didn’t turn out well for him, or the rest of the guys, because when he didn’t call her back, they got banned from Crowley’s. It goes without saying that everyone was angry with Mike, but, despite being outlaws in what was their home, Andy was enjoying the perks of his new job as a corporate lawyer. Thankfully, PJ took care of the entire Crowley’s situation when she returned home by apologizing and simply telling the Crowley’s staff that Mike shouldn’t be held responsible for his actions—he is a man, after all. These were the magic words that grant the guys access to Crowley’s once again.

An interesting twist got thrown into all of their lives when Andy hired Elsa, a gorgeous Swedish nanny, to take care of his kids. The guys were immediately smitten, but it was Brendan and Bobby who vie most competitively for her affection. In the end, Bobby won. PJ also threw a singles dinner party and invited Kenny and Mike to see if they’d be interested in any of her girl friends. Mike was less than thrilled when it became apparent that all of the girls at the party were into Kenny and not him. This was just the beginning of the romantic drought Mike experienced throughout the entire season. Luckily, this left him a lot of time to goof off.

After Mike assured everyone that he could make a shirt from scratch, he, Kenny, Brendan and Bobby competed in a shirt contest. They each had a limit of $20 to spend on materials and the results were interesting to say the least. Meanwhile, PJ decides to co-write a book with a Major Leaguer, but became frustrated when she had to coach him into keeping as focused on the writing as she was.

Then, out of the blue, something devastating happened to Brendan—he lost his DJ job. To add insult to injury, he wasn’t replaced by another live DJ—the station decided to use a computer to run his time slot. Trying to stay afloat, Brendan becomes a bartender, but is shocked at what he finds out: he’s not really good at it. He soon quit to seek other employment. He eventually took a temp job at Andy’s law firm, only to become a bit embarrassed when he ran into someone he attended college with who also worked there.

This came right around the time when Bobby dropped some shocking news on his friends. Elsa was in danger of being deported and, having really fallen for her, Bobby wanted to avoid this at all costs. So, after having only dated her for a short while, he proposed to her. She said yes, of course, because, not only is she in love with him, but once she became his wife she’d be a US citizen.

Also in the realm of big news was the huge success of Stephanie’s book, “You’re a Great Guy, But. . .” It quickly became a best-seller and put Stephanie in the stratosphere of relationship gurus. Perhaps this wasn’t as surprising after the guys found out that she used them as source material.

In what turned out to be a very revealing turn of events, Bobby didn’t invite PJ to his bachelor party. Instead, he told her to attend Elsa’s bachelorette party. Disappointed and hesitant at first, PJ told Bobby she’d go because he asked—she was a good friend. After the party, however, PJ is surprised that she actually had fun. When she reported this to Bobby, she accidentally let some other tidbits of information flow out of her mouth, like how she used to have a thing for him. She of course, still actually had a thing for him, but didn’t want to admit it. Flattered and shocked, Bobby didn’t know how to respond. The two of them kind of let it go, for the moment, at least. . .

When Kenny started dating two women at once, Mike really started to freak out about his slump. Trying to be a good friend, Andy set up Mike with his work wife, Jo, but she wasn’t interested. Instead, she took the awkward route of stating her attraction to Andy, a married man. This eventually led to Andy and Meredith going to a marriage counselor, which helped reignite their marriage.

As the stress of wedding planning got to Bobby, PJ was hanging out with Jack, his brother. Famous for his womanizing ways, things got pretty hot and heavy between the two of them, and PJ hoped that she was going to be the one that changed him. If that was to happen, it’d have to be on the lam—she and Jack agreed to keep their romance a secret from Bobby.

Despite Mike being completely flabbergasted with Kenny’s ridiculous success with women as of late, they opened a sports collectibles store, where they soon had to deal with Mexican Freddie. While he was a bit rough on the exterior, it turned out that Freddie wasn’t half the thug that Kenny and Mike assumed he was.

At the end of the season, the gang headed to California for Bobby and Elsa’s wedding. With Bobby’s dad hitting on every female in sight and his mother being as condescending as ever, PJ and Jack had plenty of diversions to use to cover their blossoming relationship. That is, until Bobby and Jack argued, fought and eventually wrestled in front of all of the guests the day before the wedding. Jack stormed off and PJ and the guys filled in the best man role he left wide open.

Even with his new responsibilities, Mike found time to hook up with a cougar named Maggie, but is disappointed when she wants nothing to do with him afterwards. He relentlessly attempted to gain her attention by acting more mature and older than he actually was, which eventually led Maggie to tell him to just be himself.

At the rehearsal dinner that night, Jack returned to apologize. Bobby accepted and, after the gang has a few celebratory drinks on the eve of the end of Bobby’s bachelorhood, they all go to bed. . .or so that was what was assumed.

It was revealed that Kenny hooked up with Stephanie and, perhaps even more shocking, Bobby knocks on PJ’s door to tell her that he thought he might be marrying the wrong woman, only to find her in her room with Jack.