Plot

Barney's plan to meet girls at the airport backfires as he and Ted are picked up by airport security. Meanwhile, Lily gets jealous of Robin.

Rather than go to McLaren's, their usual hangout, Barney convinces Ted to go to the airport with him to "pick someone up". It turns out that they're there to pick up some girls. While doing this, they fly to Philadelphia, get arrested by airport security and that's when Ted starts to wonder why he ends up in these adventures with Barney. Meanwhile Marshall has studying to do, so Lily and Robin do a girls night out and Lily notices guys are buying drinks and try talking to Robin, so Lily starts to wonder what it would be like to have her engagement ring off, and with Marshall's "blessing", she takes it off. In the end, Lily realizes that things aren't all that great with the ring off and Ted understands why he goes on these adventures/misadventures with Barney.—goleafs84

The gang are trying to decide what to do for the evening, with going to MacLaren's bar, their regular hangout, as the most likely option. The one missing person regardless will be Marshall, who has to study. Barney doesn't want to go to MacLaren's again, and promises Ted a better time - a "legendary" time in Barney's vernacular - of which Ted is suspect since Barney's "legendary" times usually means the potential for disaster. But Ted hops in the cab with Barney, unaware of where they will be heading. Barney tells him that they are going to the airport since Barney has to pick up someone. Ted had no idea that what what Barney meant is that they're at the airport to pick up girls. When they set their sights on the girls of their choice for the evening, they find out the girls are not incoming to NYC, but outgoing, heading to Philadelphia. So Barney buys two tickets for him and Ted to Philadelphia. But midair, they find out the girls of their dreams aren't quite, nor will their dream trip to Philadelphia be quite what they expected. Regardless, Marshall, feeling left out, is determined to ditch his studies and join his two buddies in Philadelphia irrespective of what they're doing. By the end of the evening, Ted realizes why he's friends with Barney despite his flaws. Meanwhile, Robin and Lily hang out MacLaren's. As the night doesn't turn out quite as Lily expected, she tries an experiment with Marshall's blessing.—Huggo

Barney (Neil Patrick Harris) decides that it is time for Ted (Josh Radnor) to get out of his routine of going to the same bar. Ted feels that McLaren's offers a middle of the road, guaranteed fun and it is safe. Barney says Ted is stuck in a rut. Promising Ted a "legendary" night (Ted feels Barney is too liberal with the word legendary), Barney pulls Ted into his cab and tells him that he needs to pick someone up at the airport. Only when they reach the baggage claim does Ted realize that Barney meant that he was going to JFK to pick up women.

Barney tells Ted that they are posing as international businessmen who have just returned from a lucrative trip from Japan. They hope to pick up women who have come to blow off steam in NYC for a weekend. Upon meeting two attractive women (Laura & one more) en route to Philadelphia, Barney impulsively purchases two tickets on the same flight for himself and Ted, and calls Marshall (Jason Segel) (who is busy studying) to tell him to join them. Barney asks Marshall to drive to Philly in his Fiero.

On the plane, however, Ted and Barney find out that the two girls have boyfriends who are players for the Philadelphia Eagles. Upon arrival, Ted and Barney are taken into custody by airport security, since they left luggage on a carousel in JFK (and then purchased a last minute flight to Philly, in cash), while video footage shows Barney doing the same thing on many occasions over the last many months. They are held for a while (Ted calls Marshall (who was on his way after Ted told him that the evening was a bust, since the girls were engaged) to come and meet them as their lawyer), but are released when Barney's luggage at JFK is revealed to contain only condoms and a PowerBar.

They then go with Sascha, an attractive airport guard, to what turns out to be a boring party. Barney, upon meeting someone who works security for the Liberty Bell, decides that it would be "legendary" to go lick the landmark. Ted initially declines, but after Barney tells Ted that he is his best friend, Ted reluctantly goes along. Later, back at McLaren's, Ted tells a girl about their adventure, and Future Ted confirms that it was indeed "legendary." Ted realized that with Barney he never got to where he wanted to go, but he always got a good story.

Meanwhile, Lily (Alyson Hannigan) and Robin (Cobie Smulders) go to the bar for a girls' night out. Lily becomes jealous of Robin because of the attention Robin receives from men at the bar. One after the other, guys hit on Robin and ignore Lily. They also buy her drinks. On the phone, Marshall reassures her that it is because she is wearing an engagement ring, and tells Lily that he would be fine if she removed it to get men's attention. Lily does so, but only succeeds insofar as a gay man approaches to tell her she sat on a grape. Robin sits in a booth alone, and happens to pick Lily's phone when Marshall calls. Marshall finds that Lily has been flirting with guys at the bar by removing her engagement ring. He turns back from Philly and goes back to NYC. Robin is annoyed by Lily's behavior, and convinces Lily that she has what most single women want: a good boyfriend. The gay man offers to help remove the grape stain, and Marshall walks in just as he is doing so. Marshall, who came only because he had second thoughts about Lily removing the ring, is reluctantly willing to fight the man, but is hugely relieved to learn that the man is gay. Just then, however, the man's boyfriend, also the jealous type, punches Marshall out.