ask sharideth: letter #8

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?




30 comments on “ask sharideth: letter #8

  1. “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.”

    that’s about the best way I could think of putting it. You’d be surprised how many walls don’t have doors on them.

  2. Brian says:

    Thank you Sharideth. You did know what I was thinking.

    • it really is the biggest fear guys have when it comes to trying to move a friendship along to the next level. and it isn’t unreasonable. ending the friendship could happen. but the truth is, allowing the friendship to stay as it is out of fear, also causes you to stay as you are. safe and frustrated. hope this helped.

  3. emikedunn says:

    Just do it.
    Ask her out, point blank.
    And don’t let her believe it’s just a friendly hang out.

    If she’s not interested in anything more than friendship, and if she’s a cool girl (and she probably is if you’re in to her) then she’ll be perfectly able to handle just moving on and maintaining the friendship.
    And if she can’t & thinks that your asking her out “ruins” the friendship – then why are we friends with her, again?

  4. jessi says:

    Well as a girl I am always flattered by a man asking me out. I’ve but a lot of guys in the friend zone but I always had and still have respect for them having the courage to ask me out. No worries…11 years..its gonna take more then wanna go on a date with me to break that frienship up.

  5. I once asked a girl, though in much more rambling words, to pray about whether God had more in mind for us than friendship. We agreed we’d pray about it, and stay just friends till we both felt like we had an answer. We both went into it with the thought and the word that we wanted first and foremost what God wanted for ourself and the other person, whether that was us or not. Nothing romantic came of it, in the end, but our friendship was undamaged and she’s still one of my favorite people. We had some interesting conversations along the way about what marriage meant to each of us, what our flaws and hangups were, what our thoughts were about life and faith and children and even which direction you roll the toilet paper, though the latter was more in jest, by way of examining obstacles to a happy match between us.

    Not that I recommend everyone to bring up marriage as a way of opening the relationship discussion. 😉 You can seriously freak a girl out with the pressure that subject can bring up. It fit the way she and I interacted though.

    • yeah, i don’t recommend leading with marriage either. unless you want to freak her right out.

      • Indeed. 🙂 It does bring up the point of the way you ask being in line with however your relationship normally works with awkward subjects. Launching right into it fit our particular pattern of relating to each other after a decade of friendship; the way someone else asks need to be in keeping with their own normal patterns.

        I’ve long ago accepted that I am not likely to ever be considered normal. 😀

  6. dtdorrin says:

    Just go for it! You have no idea how many times I’ve heard single girls talk about how guys seem oblivious to all the awesome women right in front of their face. Most of the time because the guys seem too distracted by waiting for their perfect girl to appear out of thin air with a chorus of angels singing in the background as an introduction. My point being, you could be one of those guys who DOES realize something great is right in front of him.
    Not to mention that this sounds like the makings of a 90s Tom Hanks movie. Bonus!

  7. bAnnanana says:

    I put a guy in the friend box for a year. We’re now in a very happy relationship. As in *coughlovecough* ahem. I can’t imagine being with anyone else, ever again, and I don’t know why I didn’t know better when I settled for dating other guys.

    But I’ve had other male friends who asked me out who couldn’t be more than friends, I went on a date or two with them to make sure how I felt. And we’re still friends, except that one that I know still looks for that “door” whenever we come into contact. Awkward.

    I personally don’t see any reason for the friendship to be ruined because you see if she could like you. Unless you’re the type who won’t actually want her friendship if you’re rejected. Or unless you’re only her friend because you want there to be more. Or if she’s crazy, in which case, you’d be lucky to get out of that.

  8. kelybreez says:

    I’m a guy. And I’ve been married 21 years. So I have no advice.

    Except, to not marry a good friend is the dumbest thing I’ve ever heard of. If you and your wife don’t end up friends, you’re gonna wish 448,754 times every day that you were best friends.

    I swear on a stack of Leif Enger and Wendell Berry novels that the BEST part of being married is gonna be laughing with her. (Read Jayber Crow by Wendell Berry to see what it’s like to miss marrying your best friend.)

    If ya ain’t laughin’, it’s gonna be a LOOOOOOONG marriage. Or worse, a short one.

    Which is to say, Who in the heckubus else would you marry, if not a great friend?

    Besides, she might just think the same thing.

  9. Brian says:

    Thank you Sharideth for answering my question. After reading your other posts, you’re very credible to me. Ruining was my friendship was my biggest fear, and you put things into correct perspective for me.

    Thanks to everybody else for your comments. Each comment was very encouraging.

    I think I’m going to “just ask.”

  10. Chris says:

    Is it too nosy of me to encourage Famous Brian to report back?

  11. Credible or otherwise, Sharideth, you got it right. Even a blind squirrel gets a nut sometimes.

    Best of luck, Brian!

  12. Brian says:

    I just thought I’d give an update.

    I never got around to having this conversation with her until today. What happened today was totally by accident. She made a comment on a blog , and I knew it was immediately about me. She didn’t know I read that particular blog.

    She’s not interested in me. She never has been. She still very much values our friendship. She’s known I’ve been interested in her for about a year. (For the record, she did not say anything cruel. She was not panicing. She spoke with grace even though she didn’t know I was reading) .I need to work on my poker face.

    So here’s what our friendship in the future will be like: not much different than the past 11 years.

    Surprisingly, I’m not sad. I’m not heart-broken. I’m not even disappointed. I’m actually a little relieved.

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