In the series premiere, Dana is determined to succeed in New York in both business and love, while Peter is perfectly content to go on dating his way through it. While it is the streets of New York that offers this duo a first glimpse of each other, it's family and friends who conspire to set them up. The audience will go along for the ride as they venture on their first date and hear exactly what they really think of each other.

Things become awkward between Dana and Peter when she runs into him on a date with another woman; Amy pushes Dana to see other people.

After learning that Peter is attending Amy's dinner party with a date, Dana asks her new, attractive boss to accompany her.

Peter and Dana's plans for an intimate evening go awry when their reservation at an upscale oyster restaurant is pushed; Amy and David make a major decision.

After a fight, Peter and Dana's friends try to help them smooth things over with a romantic movie but the plan backfires; William wants to hunt down his biggest critic; Dave and Amy revisit their first fight.

Dana is forced to reveal an embarrassing a hobby to Peter.