Join Jen for three especially romantic Valentine's Day dates, as she and the remaining men - John Paul, Jerry and Ryan -- travel for overnight trips to the Fairmont Southampton Hotel in Bermuda, Daufuskie Island Resort outside Savannah, Georgia, and Chatham Bars Inn in Cape Cod. Jen and John Paul fly off to Bermuda, where they fit in a Jet Ski ride and picnic on the beach before it starts raining and they have to head for cover. Things turn serious when they imagine what their everyday life would be like together, as they enjoy a romantic dinner on the beach punctuated with a spectacular fireworks display. A relaxing and idyllic date awaits Jen and Jerry, as they spend time at the Daufuskie Island Resort, where they picnic, play croquet and take a spin in a horse-drawn carriage. Things heat up when Jen challenges Jerry's sincerity - and admits that it has been bothering her lately. Finally, Jen and Ryan cozy up to one another in Cape Cod, sharing a romantic chat atop a lighthouse, where they address Jen's awkward visit with his parents. Later they snuggle up by a fire and have a romantic dinner on the beach. As Jen heads into making another difficult decision, the men are surprised to find out that she feels she needs just a little more time with each of them in some last minute chats. Then, Jen must present roses to only two of the three remaining men.