The Wing Man is a story about three friends who work together in a record shop: Jack Vedder: Care-free and over-confident with a penchant for trouble. Jessica Gargiulo: Gorgeous, silver-tongued and feisty. Kyle Julien: Shy guy who goes with the flow. SPOILER ALERT! Jessica, fed up with Jack’s careless behavior (“You slept with Mindy and didn’t call her back? I am such an idiot for introducing you to her!”), threatens to call every number in Jack’s little black book and ruin his chances of ever getting laid again. Jack, determined to make things right with Jessica, encourages Kyle to ask Jessica out. Kyle has always had a thing for Jessica. When he finally works up the nerve to ask Jessica out, Kyle finds out that Jessica has a boyfriend: Morgan Jeffries: Handsome alpha-male, asshole. Now, Jack has both Jessica and Kyle mad at him, but not to worry — Jack has a plan. Jack and Kyle meet Jessica and Morgan at Streets of London Pub. Jack distracts Morgan while Kyle moves in on Jessica. Well, this plan doesn’t go…as planned. Jack does manage to pull Morgan away to the bar, and Kyle and Jessica do get a chance to talk, but Morgan soon returns and demands that he and Jessica leave. The next day, at work, Jack tells Kyle that he saw Morgan hitting on the bartender. That guy, Morgan, is a real jerk, so Jack hatches the ultimate plan to get him out of the way for good. Actually, it’s not the ultimate plan. It’s a terrible plan, as Kyle points out, but he goes along with it anyway: The Plan: Jack wants Kyle to make a big, romantic gesture to Jessica on Valentine’s Day — by giving her a dozen roses. Kyle, afraid of a confrontation with Morgan (“It might be awkward if I knock on her door and her boyfriend answers.”), is hesitant to agree to this. Jack convinces him to play along by dressing as a delivery man (“I can say I have a special delivery, then you jump out with the flowers!”). Jack and Kyle show up at Jessica’s house on Valentine’s Day. Jessica is visibly upset. She’s just found out that Morgan’s married and has left her to go back to his wife (seriously, what a douche!). Luckily, Kyle is there, with the flowers, to console her. It all works out. Kyle and Jessica end up together and Jack is a better friend.