i think the better approach is do it as a group. with the team, a chunk of it, or a few friends. want to sit with "us?" want to run with "us?" "we" think you could use a friend. maybe get the nicer guys involved. gets at same issue, better chance of a natural friendship, less about you in particular. to me you're better off bringing him a group with some genuine "friends" (plural) as opposed to "pity."
what could be misunderstood, XC girl and i, would sit together many meet bus trips, got along well, joke, tease, she has a pet name and song for me, she and dad cheer for me at XC and TF meets, visit her locker almost daily and walk her to class, introduced to her dad, dads knew each other, finally second XC season says, "ask me out and i'd say yes." wanna go to the movies, yes. hears through the runner grapevine i am all excited, "oh, but i meant as friends. maybe i'd grow into it, though." she kept trying to revive the friendship after, stop me in the hall and want to catch up, but i checked out. was a shame, it was fun. some mix of that would be where the guy will think you're interested.