okay so it’s not really a letter. it’s a single question. but it got asked, so i’m going to answer it.
How the heck do you ask a close friend of 11 years out on a date? Serious question…~Brian of Comment Fame
here’s my serious answer, Famous Brian.
you just ask.
if you have known someone that long, you should have a close enough relationship to simply say hey, “what do you say about letting me buy you dinner on friday?”
stop freaking out. breathe. i know what you’re thinking…
“what if she says no and hates me forever for ‘ruining’ our friendship?”
so what if she does? at least you’ll know and you can stop beating your head against that particular wall and move on to another that might actually have a door.
the truth is, if she says no, it will be awkward for a while, but if you are truly friends, she will eventually get over it and you can joyfully skip back down the path to Platonicville.
but if she says yes…
you just might have the makings of something that other people will envy for decades.
there is a door number 3 though…
it’s a bit more subtle. you can just start taking her out without calling it a date (just make sure you pay). eventually you’re going to have let her know your ulterior motives and then you’re back to option #1. however, there are 2 things you need to weigh against each other before trying this approach.
1. this could solidify your permanent residency in the friend box. it’s a big risk. if she thinks it’s “safe” to be with you alone and doesn’t consider it dating, you’re pretty much screwed.
2. if she is into you, the subtle approach can provide an organic way to make your move.
a friend of mine was telling me that a girl he wanted for years had just gotten married. he was all mopey and “why did she marry him?” blah blah whine blah. my answer to him, “if she’s married and you did nothing to let her know how you felt ahead of time, you blew it.”
harsh? yes. but true none-the-less. turns out, she’d wanted him, too. something he found out a year after she got married.
moral of the story? when it comes to love, especially with someone you know so well, leave nothing on the table. the risk is worth the reward. oh yeah, i’m geting all cliche’ up in here.
for some added wisdom on getting her to think of you as a man instead of her girlfriend, read this.
okay readers. you guys are always good at this stuff. what would you tell our friend, Brian?