Phillip and Lauren met on June 6, 2008 and their first date was at a Tom Petty concert. The two were introduced on JDate, an online dating service, and chatted for weeks prior to their first date. Luckily they chatted when they did because Phillip was ready to give up on JDate prior to speaking with Lauren. Following their first online chat, the two spoke regularly in the evenings via an instant messaging service. Their first date took weeks to occur because Phillip was on business in Panama City. By the time they met for the first time, the two already had two dates planned, one to a Tom Petty concert, and the other to a R.E.M. concert.

On the evening of their first date, Phillip took the metro to meet Lauren at one of her friends apartments. The concert was a fun event planned by Lauren Breitenother and involved a pre-party and party bus prior to the concert. Lauren and Phillip hit it off from the beginning. Melissa later commented that when she first was introduced to Lauren and Phillip that evening, she thought that they were a well established couple.

The first date went well and so did the second. The couple both sang unabashedly and aloud at the R.E.M. concert. At the concert, Phillip got to meet Josh Caplan, one of Lauren's very good friends.

Soon thereafter, Lauren invited Phillip out to her grandma's birthday party at Chiparellis, a family favorite in Little Italy, and Phillip met Laurens parents, Lois and Neil. Lauren and Phillip continued to date, and at Thanksgiving time Lauren traveled to Florida with Phillip to meet his family, father Howard Berkowitz and his wife Debbie, mother Rise Page and her boyfriend Karl, and brother and sister Joe and Allison. She also got to meet some of Phillip's best friends, Ryan Faircloth, J.R. Halaz, Matthew Perry, and Kiley Blake.

Although there were about 50 miles between their residences, Lauren and Phillip did not allow that to get in the way of their dating. Lauren and Phillip enjoyed having double dates with her roommate Amee who had also met a guy that lived in the DC area. Lauren and Phillip attended Amee and her husband Kevin's wedding over Memorial Day Weekend 2010.