Ask Jono: Super-Casual Dates
I was hoping for some male perspective on this situation I have. I met this guy through a school sport. We’ve talked a few times now, and I’m really starting to fancy him. One of my good friends is dating one of his good friends and through this connection I heard that he thinks I’m pretty (amongst other positive things). So, now I’m at a loss for what to do! I want to know him better, but not I‘m not sure how to go about that. He’s not in any of my classes since he’s a year above me. I see him in the hallways sometimes but I never say hi or even make eye contact because I don’t want to creep him out...
I realize that walking up and saying "hi" out of the blue might be intimidating, but I really wouldn't worry about eye contact creeping someone out, unless it's the kind where your eyeballs literally make contact, in which case you have already done quite a few other things wrong. I think most guys find most attention flattering, particularly from someone they find attractive. You are cleared for approach.
What you might be asking is literally just, "How do I walk up to a human boy and say hello with my mouth," in which case all you need to do is stay frosty and behave like you're approaching him for some totally mundane reason. Further advice here and here. If you want to invite him to approach you, using your face, Auntie has nailed this one. So hopefully those things will get you started, and I'm going to focus on the next part—what to actually do with the dude to get to know him better. I know that everyone has different comfort definitions on what constitutes a "date," and I know some parents are way more restrictive about this stuff than others; some family situations are all "No daughter of mine is going out with a boy unless I'm in the parking lot with binoculars!" and in others, you can just be like "Dad, I'm taking the bus to Drugsburg," and dad goes "Ehh" and waves dismissively from his hammock. So I'm going to try to give you options that parents are unlikely to object to. If I use the word "date" from here on out, I mean a totally platonic cutesy situation, not exchanging ravishing gazes over candlelight at Le Unpronounceable French Restaurant.
I'm throwing this out there first because do you even realize how much lower-stress this is than going to a movie? If you just go for a morning jog together, there's absolutely no point at which you are expected to put your arm around the other person and lean in for a kiss, unless you are jogging in an extraordinarily wrong way. WARNING: Do not attempt this if one of you is in terrible shape, because it is humiliating. (I also assume that since you two play the same sport, you could simply practice that with him, unless your sport is, like, wrestling, in which case noooo.)
High School Football Games? Wallyball Games? "Footie?"
Going to football games is one of those things that everybody at my school did, even people who detested football, because it was a big social event like a dance without the part where people were actually required to dance. However, you did say that you "fancy" this guy, so perhaps you are British, in which case you'll have to substitute something they do across the pond. Watch humans kick a ball, ideally with other people.
When I was in high school, bowling was universally acknowledged as stupid and we all allegedly hated it, but now that I bowl a lot, I constantly see high-school-aged couples there on very laid-back dates. It looks like a perfect combination of getting to know somebody and having fun, and I really wish I had thought of it earlier, instead of the very many terrible things I did think of. (Braveheart as a date movie? Was I medically insane?) Of course, sometimes the dude is completely into his bowling, going, "OOOH, STRIKE! EAT IT!" and really trying to annihilate his date at bowling for some reason, and it is embarrassing. This isn't the norm, though, and I feel like these casual non-sports are a perfect idea.
Anything Else That You Would Do With a Friend
Seriously, just pick something that you would be comfortable doing with a friend and try to get him to do it with you. Go hiking. Go volunteering. (This sounded like a terrible idea when I first heard it, because nothing is less romantic than having a man at the soup kitchen ramble incoherently about the lizard man conspiracy, but being in a trying situation together definitely shows you what someone's really like.) Heck, go to church, if you both do that; just be careful about coming off mega-religious if he's definitely not. The whole point is that if it's something you'd enjoy more with one of your friends, then you should enjoy it more with this guy along, too. Approach it that way, rather than as A D-D-DATE, and you'll find there's a lot less pressure for both of you.