Welcome to the Sidebar’s advice column, where Mike, Mike, and Mick alike sit down for a chat with our very own Muffle. Her advice might be bad, but hey, at least someone’s listening. Today we’re talking about crossing the Rubicon between friends and more-than-friends.

Hey Meezy,

How bad an idea is it to ask out a friend when I’m not even sure how interested I am in serious dating at the moment?  I’m not sure how much I really want to date anyone right now, but my friend is cool, and I know she won’t stay single forever, and I’d like to give it a shot.  That said, I don’t want to hurt anybody, either.  Should I just go for it, or let things be?

No Said Date

Oh man, there are so many reasons this can go either way!  You’re pretty sparse on details here, NSD, so I’ll do what I can to lay out the equation you’ve got to do in your head in this situation.  Here are your variables, with the weights I’d give them if I were you:

  • Your friendship.  How close are you to this person (let’s call her Thelma because that’s almost definitely not her actual name)?  Is this a friendship that you rely on to get you through thick and thin, or an acquaintance you see out with a group every so often?  If things were to get weird with Thelma, would it mess things up with your other friends?  Let’s give this a score between 1 and 20, with 1 being that Thelma is your friend since infancy who nursed you back to health when you caught malaria from that ill-advised spring break in Burundi and 20 being a girl you saw at the bodega one time.  (On this scale, the lower the score, the more Thelma matters to you as a friend.)
  • Your romantic feelings.  You note that Thelma is “cool,” but you don’t tell me anything about how you feel about her.  Do you think she’s sexy?  Alluring in an intellectual way?  Something deeper, or something shallower, or what?  Let’s rate this one out of 10: 1 is what you feel for any human being who is of the gender you find sexually appealing, and 10 is Angelina Jolie in that terrible Beowulf movie from 2007.  Don’t pretend you don’t know what I’m talking about.
Your mom’s hot, Grendel.
  • Your aversion to serious dating.  It sounds like you’re not sure you’re ready for the commitment a serious relationship takes, and that’s a fair thing to question, though it’s important to note that dating doesn’t have to be all-in; it’s just something you need to communicate about very clearly throughout the relationship, to make sure that one party isn’t way more invested than the other.  Let’s rate this one out of 10, too; 1 means you’d rather bungee jump with the cord attached to your genitals than enter into a formal relationship right now, while 10 means that you’re looking to be married in the next 12 months.
  • Miscellaneous.  There are a bunch of other factors that come into play here that only you know, e.g., how likely Thelma is to continue being your friend if you try to date and it doesn’t work out, the likelihood that this is your one shot to be with her, any other influences like whether you have other close friends who have dated her and that would make it weird, likelihood that she says no and makes this whole question irrelevant, whatever.  For each factor that weighs in favor of dating her, add one; for each against, take one away.  Let’s move the needle up to 5 points here.

Now add ’em all up; if you’re at 25 or up, I say give it a shot.  Boom, done.  Mission accomplished.


The caveat here is that the above is all nonsense; it’s just a way of trying to get you to think about your feelings and weigh them objectively.  If you feel disappointed by the answer you got by doing the math, then that’s your real answer right there: now you know what you really wanted to hear, and you can go forth with the confidence that whatever happens next, at least you did what you thought was right.

Snark and tipples,


Got a question for Muffle? Send it to mufflemayi@gmail.com.