Playing the middleman had never been Jesse's thing.
Why would it be? After all, he'd never exactly been the kind of person who cared very much about anyone else's romantic relationship. But Blaine had asked him, and asked him very nicely (as opposed to his typical phone calls of "ST. JAMES GET OVER HERE NOW I NEED TO PUNCH SOMETHING AND YOUR FACE WILL DO JUST FINE"), so who was he to refuse?
They had a very strange relationship. Don't worry about it.
Either way, he'd ended up a part in Blaine's master plan to set up his ex-boyfriend, Kurt, with someone else. Jesse thought it was quite nice of Blaine to care, though he had to admit that being set up by someone with whom you had a failed romance could lead to potential issues. But that was before he realized just who Blaine was trying to set Kurt up with.
He remembered Sam Evans. Of course he did; they'd spent nearly two hours together at Breadstix the night before prom the year before. Sam had been nice, a little goofy and shy, though Jesse had been a bit more focused on Rachel than he had on Sam. But he had liked Sam, decided that the boy was very nice, and had appreciated it very much when he'd stuck up for him later on when he'd been brought in as a glee club consultant.
So he had no qualms whatsoever "dropping by" and taking Sam out on a "man date" with the sole purpose of talking his ear off about how awesome Kurt was (Blaine had given him a list that was five pages long, which Jesse had promptly thrown in the trash because, really?) while Blaine did the same with Kurt.
The surprised look on Sam's face was a definite perk, too.
"Um, okay," was all he said before following Jesse out to his car. When the other was safely in the passenger seat, Jesse locked the doors and asked, with no warning, "Are you gay?"
Sam tugged on the handle of the door, briefly meeting Jesse's eyes before managing to get out a nervous, "No, Jesse, I'm not interested in you."
"So that's a yes," Jesse concluded, beaming. "And stop acting like I'm kidnapping you." Sam stopped tugging on the handle, looking over at Jesse again, confused. "I'm not asking for myself."
"Who, then?" Sam's hand left the door of the car, looking at Jesse with curiosity rather than confusion now. Jesse smirked.
"How would you feel about a certain mister Kurt Hummel?"
The embarrassed smile that crossed Sam's face was answer enough.
"Come on," Jesse put the car into gear. "Let's go crash his and Blaine's man-date, or whatever it's called when your ex boyfriend tries to get you to admit you like someone else. I think you'll be much more persuasive in person."
Jesse couldn't help but laugh when Blaine caught sight of him and Sam walking towards him and Kurt a few minutes later. Blaine had planned the whole thing out down to the minute, telling Jesse that they were to "accidentally" bump into each other when they both just so happened to suggest going to see a movie. Except now here he and Sam were, walzing (okay, he was strutting and Sam was shuffling) into Breadstix, making a beeline for their table, Jesse smirking and Sam smiling shyly.
"Why hello there," Jesse said loudly, making Kurt jump and turn around. "Fancy running into you fine fellows here at Breadstix. Budge up, will you?" He slid into the booth next to Blaine, elbowing him to make him scoot over, watching as Sam asked quietly if it was all right if he sat down next to Kurt. The way Kurt blushed when he slid over and said that yes, he most definitely could sit down, was proof enough that no matter how glaringly obvious Blaine might have been, it had either worked like a charm or Kurt had already liked the other boy for quite some time.
Probably the latter. Blaine wasn't that convincing.
"Oh! Goodness me!" Jesse suddenly exclaimed, clapping a hand to his cheek. "I have forgotten that I left my oven on. My whole house is going to burn down if I don't stop it. Blaine," he grabbed Blaine's arm and yanked, "you're coming with me."
Jesse hauled Blaine out of his seat, winking at Sam and giving Kurt the thumbs-up before dragging the shorter boy to the door.
"Glaringly obvious much?" Blaine asked, once the door had swung shut behind him.
"Well it worked," Jesse shrugged, peering through the glass to see that neither Kurt nor Sam had moved to sit opposite each other, but where still sitting rather cozily in that one side of the booth. "See?" He grinned at Blaine. "Admit it. I'm awesome."
Blaine rolled his eyes.
"Come on," Jesse grabbed Blaine's hand, not waiting for the exasperated remark that was no doubt dying to be said. "Let's you and me go to that movie instead."
"Are you asking me out on a date?" Blaine looked over at him, raising an eyebrow.
"Think of it more as fulfilling the dream you've been having since you met me," Jesse corrected. Blaine rolled his eyes again, but then he smiled.
"Well if that's what you're doing, then you're paying."