Dear Jono,
I come to you with a question of social acceptability. You see, there is this boy. He is a senior, and I am a junior. We've gotten to know each other somewhat recently; we've been talking a lot and he has asked for my number. Friends (to whom I haven't told anything) have told me that he seems interested. Seems fine and dandy, right? Eh...not so much: he is an ex of my sister.
From that detail, I know all signs point to "NO DON'T DO IT!," but just hear me out. This happened two years ago. My sister was a senior (she's now away at college) and he was a sophomore. They had been friends, tried dating for about a month, and then she broke it off. They remained on friendly terms, and my sister has had two serious boyfriends since, one which she is currently dating. So, I face a dilemma. Should I stop things where they are and not allow it to become something more? Or go for it? I've only had one boyfriend, two years ago; chances like these do not come often for me. Please advise me.
I appreciate how you sort of eased into the big reveal there. You probably expected me to read the first few lines, nodding and sipping my tea, then get to the huge twist and go "YOUR SISTER'S EX?? PTHHBT," and do a spit-take all over my monitor. Well the joke's on you, because I already do that all the time anyway. I suppose you're right to be concerned, because most people would react to your proposition by chasing you away with a broom. Luckily for you, I have pretty forgiving sensibilities as far as romantic norms are concerned, which is a polite way of saying I am super-lazy and will let people get away with pretty much anything. There are some considerations to keep in mind here, though.
First off: his intentions. As far as I'm concerned, there are two types of guys in the world: guys you can trust to stick by you, and guys who just end up wandering the alleys at night, pawing through my garbage and meowing until the early hours of the morning. I guess at some point I started thinking about cats there, but I stand by my distinction, and I assume you've given thought to whether or not this guy is A Good Guy. Furthermore, I'm assuming you feel that he's interested in you, not in the blockbuster sequel to your sister. I don't think I even need to explain that taboos about this sort of thing exist for a reason, but since lots of women seem to suffer from Jerk Blindness, I will belabor the point: if he ever accidentally calls you your sister's name, file him alongside guys who wear bandanas but no shirts, and move on with your life.
I think you probably realize all of that, though. So if you still want to go ahead with this, here's how to do it.
1.) Talk to your sister
I am not entirely sure how this works with women. With guys, one might say to the other something like "Sooo... Angela," (where Angela is the name of the other guy's ex, and not some kind of Man Code) and segue into seeking approval to date her, without having to actually ask outright. Then maybe they'd turn their hats backwards, play Call of Duty, punch each other a few times, and wow I kind of hate these metaphorical guys so let's just move on. However you do it, approach your sister; it's not absolutely required for you to get her approval, but it will make things much easier. And besides, maybe there's some unspeakable secret reason that she broke up with him in the first place. ("Every time we make out, steam shoots out of his ears! It is a serious medical condition.")
2.) Prepare for some awkwardness
Look, every relationship at your age is already a goofy awkward mess, all "where should I put my hands" and "uh oh now what do I do" and "OH NO THAT WAS COMPLETELY THE WRONG THING" followed by frantic re-adjustments and then elbowing your girlfriend in the nose. Or so I am told. My point is that the odds are already heavily stacked in favor of things turning stupid; with this added complication, you should be prepared for more than the usual turbulence. The society page will be all abuzz with the scandal of you dating a sibling's ex, monocles will pop off the faces of wealthy aristocrats, and dowagers will faint in the streets left and right. Or none of that will happen, but preparing for the idea that it might is a good way to judge whether or not you want this.
3.) If it works, stick with it
Ultimately, though, who really cares about all that? Maybe your sister gets all huffy about it, and you get in a fight, and all she gets you for Christmas is a bucket of pine cones. So what? People make up. Maybe the guy's parents keep forgetting which one you are and just start confusedly calling you "champ" and "buckaroo" and "hey there." None of that really matters in the long run, and even if this whole thing just collapses into an embarrassing wreck of sibling rivalry and mistaken identity, at least it's relationship practice. And if it does last, the only thing that matters is that you're happy, which is worth, like, ten buckets of pine cones.
Do you agree that LW can go for it?
Related post: The Pros of Having Older Siblings
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