Reader question # 65: How do I ask out a friend of a friend who lives in another city?

Dear Captain Awkward,

I’ve got a thing for this guy who I met through a mutual friend. He lives in another city so I don’t see him all that often [it’s close enough that a lot of people date (and non-romantically commute) between the two cities, but far enough that casual hanging out with friends can be difficult]. We’re fairly friendly on Facebook and the like though, which has kept the infatuation going.

Mutual Friend thinks we’d be perfect together, but she refuses to find out if he might be interested in me [because she is also awkward?]. I’ve reached the point where the fun of having a crush has worn off and normally at this stage I’d just go ‘fuck it’ and get a good friendship out of the deal – but that is probably why I am perpetually single with a lot of really amazing friends. I feel like I should be proactive about this and actually do something, but my issues with that are as follows:

  1. I’m not sure that it would be a good idea to start something with this guy as Mutual Friend is really important to both of us and it would add an extra level of awful if things went wrong [basically the ‘But what if our friendship is ruined!’ excuse, but with an extra person].
  2. As I don’t actually see him very often I may have built him up too much in the ‘Oo, crushes are fun!’ stage, breaking rule #2 of the Rules for Geek Dating and increasing my levels of intense awkwardness.Case in point, I am writing a multi-paragraph letter to an advice column about a guy I hardly know.
  3. I’ve got no idea when I’m going to see him next, but it is probably not for awhile, which means if I am going to do something it will need to be over the internet.

So my questions to you are:

Should I go for this? It seems like really flimsy grounds to possibly start a lot of drama on.

If I do go for this, is there a way to indicate your interest to someone via Facebook message without it being super weird? Particularly someone who you’ve never hung out with one on one? I’m one bad day away from sending a message that reads “HEY I THINK YOU ARE GREAT AND MAYBE WE COULD HANG OUT SOMETIME BECAUSE THAT WOULD BE GREAT, BUT IF YOU DON’T WANT TO THEN THAT IS GREAT TOO AND WE CAN JUST PRETEND THIS NEVER HAPPENED. K THX BYE.” And that would not be attractive to anyone.


Hello, you didn’t pick a snappy nickname, so I’ll pick one for you:


There is a reason your mutual friend will not “find out if he likes you” – it’s because you are all over the age of 15, yes?  So (s)he is generally encouraging, but wants to stay out of the middle and wants you to handle stuff yourself.  That seems like a pretty great idea and not awkward at all. But where does that leave you?  It leaves you just asking him out already.  Here you go:

Option 1:  “Dear ____, can I buy you dinner next time you are in town?  I’d really love to hang out with you.

Option 2:  “Dear ____, I’m going to be in (your town) the weekend of (date).  Can I buy you dinner or brunch one of those days?

I know, I know, it feels like there is so much at stake, but I refuse to believe that any friendship, including the one with your mutual friend, is so fragile that it cannot handle that question.  I can’t remember the last time I dated without using the internet as a go-between, but in the olden times I think people met each other through other cool people they know and having friends in common was a reason in favor of a relationship, not a reason to avoid one.

If he says no, the distance is actually an advantage, because a lot of time will go by until the next time you see him and the awkwardness will wear off with time.   Then you’ll run into him via your mutual friend, and you’ll look all cool and unapproachable and gorgeous.  He’ll say “Hey” and you’ll say “Hey” and then you’ll ask him a question about something totally unrelated to show that you’ve let it go, and it will never come up again.  If by some unlikely fluke he avoids you forever, then you have just found out that he is a Giant Rude Awkwardpants and you didn’t want to date him anyway.

It’s hard to get into any kind of dating thing going if you can’t say out loud that you’d like to go on a date.  Multiply this by 1,000,000 for a long distance relationship because if this turns into an actual thing, both of you are going to need to use your words via Skype/phone/email/text. You might as well get the e-flirtation going now and see if you can relate on that level.
Fortune favors the bold.  Do it today!
  1. Stephanie said:


    I think this exact quote (notice where I stopped quoting) is EXACTLY what you want to say. “Hanging out” can mean whatever your intended wishes it to, from having a cuppa to happy fun naked time if it gets to that.

    Being the one to say “you know, you seem pretty cool and I would like to spend more time with that” is kind of going out on a limb, but really, if someone said that to YOU? Would you be angry? You’d probably be flattered, if nothing else.

  2. Charo said:

    Agreed. I’ve recently stepped back into the dating pool, and yeah, it is really scary to go out on a limb for the first time, especially with a friend or friend-of-a friend. But it’s do-able. And it gets easier the more you put you put yourself out there. Besides, what’s the worst that could happen? You get what you want because you had the guts to ask?

  3. Caito said:

    I had this situation a couple of months ago. I actually did the “Oh hey, I’m going to be in your town for some reason, so if you’re free, want to grab some coffee while I’m there?” Coffee turned into dinner, but not a full-fledged date. I wanted to ask him out then, but I was too shy to do it in person. So I asked him out via internet a couple of days later by saying, “I enjoyed the other night, and I have to admit to having a bit of a crush on you. May I take you out on a proper date sometime?” It worked.

    I don’t know how I’d have handled rejection (if that had happened) but hiding behind the computer made it feel like I had a safety net.

    And he asked me what the whole coffee-dinner thing was, if not a date – I told him it was a “platonic dry-run.” Just to make sure we had chemistry outside a group and off of Facebook.

    We met through mutual friends too (a couple – I’m friends with the wife, he’s friends with the husband), so one of our date conversation topics was who would get custody of them in the case of an awkward bad break up. (I get them for most of the year, but he gets them for holidays.) (Except actually we are still dating, so.)

  4. k said:

    “I know, I know, it feels like there is so much at stake, but I refuse to believe that any friendship, including the one with your mutual friend, is so fragile that it cannot handle that question. I can’t remember the last time I dated without using the internet as a go-between, but in the olden times I think people met each other through other cool people they know and having friends in common was a reason in favor of a relationship, not a reason to avoid one.”

    Yes. Yes this is a perfect paragraph. LW, you’re trying to control this situation and all of its hypotheticals way too far into the future.Look, the truly scary and also superexciting and awesome thing about getting to know new people and dating them is that you can’t know what will happen!

    You’ve just got to jump into the deep end of the pool and ask him, even though you might date him or you might not date him or things might be complicated vis a vis mutual friendships or perhaps you might step in front of a bus tomorrow morning and end up in the hospital, or maybe he’s actually allergic to cats which is totally a dealbreaker for you. If you don’t ask you’ll never get to find out.

    Basically the only situation where you know what will happen in your love life is if you never ask anyone out. Then you are pretty likely to stay single!

    Just go for it, seriously.

  5. denelian said:

    a thing…

    mutual friends either A) are actually your friends and won’t abandon you if something goes wrong with you dating a DIFFERENT person or B) aren’t really your friends.

    i discovered this [by finding out i wasn’t really a person’s friend, actually. i know, what a rat-bastard i am. in my particular case, it was a friend who wanted to date an ex-boyfriend – this thing that is supposed to be a Rule You Don’t Break. i didn’t *care* if they dated – i just explicitly stated that *I* was not involved. and when i held that line – it sucks enough to break up with someone; i wasn’t up to “helping” her cope with breaking up with the guy who broke up with me – suddenly i was an Evil Bitch who had Never Been Her Friend and etc. there CAN be issues with dating friends of your friends – but so long as you leave the FRIENDS out of it, it should be fine. no, really – unless you have no other friends, you don’t take the bad stuff to the friend you have in common with the person you are/you want to date. if you can follow THAT much more sensible Rule, i think you’ll be very pleasantly surprised.

    and good luck!

    • JenniferP said:

      Oh, you make a great point – if the Letter Writer and the guy DO hit it off (or don’t, whatever) the mutual friend is NOT THE AUDIENCE for the ups and downs of the relationship. That’s how you ruin friendships, not the dating-friends-of-friends part.

      • denelian said:

        yes – at least, IME that’s how you ruin friendships.

        of course – i’m not a fan of “drama”, so i’m probably not the friend to drag into things. i’m the friend who’s shoulder you cry on, that you go to to hear “you’re incredibly awesome and s/he’s an idiot for not seeing that”. so i’m maybe not the *best* judge, because i know some people do enjoy being dragged along for the ups-and-downs. but unless they want to be, and TELL you that they want to be, including the friend who introduced you just isn’t fair.

        i TRY to be helpful 🙂 i don’t know if i suceed, but i TRY [i feel i owe it to you and other commenters, since you guys helped me so much!]

        • LongdistanceLW said:

          That actually helps a lot, and I feel silly for not having thought of it.

          • denelian said:

            oh, don’t! *most* people don’t think of it – i didn’t think of it until i was stuck in the middle of someone else’s relationship. but i think it’s something we should be, not just *doing*, but spreading.

            seriously – GOOD LUCK! i hope everything goes as you hope!

  6. denelian said:

    erm – that “unless you have no other friends” was NOT meant to make it sound like YOU, LW, had no other friends – but i have 2 friends who’s only friend is ME. and they wanted to date. and thank all the gods that it worked, unlike the other situation i described – my problem with the first scenario is that i WASN’T the only friend and it was cruel to try and drag me into it when she OTHER FRIENDS who weren’t emotionally involved. in the second, i’d been trying for YEARS to get these two to get OTHER FRIENDS. i introduced them, not thinking that they’d… hit it off so well [it’s D’s fault, for never telling me he’s bi. i’d have been a bit more prepared if i’d know that 😀 ]

    ok, now i’m just babbling.

  7. LongdistanceLW said:

    Thanks! There are several factors that I didn’t include which make the over-thinking more understandable, but having to boil it down to the salient points and getting reasonable advice from unbiased people has helped me dial back the crazy.

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