Dear Kate: I think I’m in love with my best friend. Should I tell him?

Dear-Kate-column-identityBy Katharine Luckinbill

Dear Kate,

There’s this guy that I have known for quite some time. Actually since primary school and we’ve always had a very special friendship. Just a little while ago I started to realize that I felt more for him than just friendship and I think he maybe feels it too. Should I tell him how I feel and date him? Or is dating a good friend a bad idea?


Mixed Feelings


Dear Mixed Feelings,

I have been in your shoes, and boy are they hard to walk in! Kudos for thinking it through before making any rash or hasty decisions though.

In my (humble) opinion – this could go one of three ways.

  1. You tell your best friend that you adore him and want it to be more, and he feels the same way, and you get married and have beautiful babies and live happily ever after, forever and ever.
  2.  You tell your best friend that you adore him and want it to be more, and he feels the same way, and you get into a relationship, and it’s really not good and it explodes in both of your faces and you can’t really go back to being friends because now you’ve seen each other naked (and everything that comes with that).
  3.  You tell your best friend that you adore him and want it to be more, and he totally does not feel the same way, and you go through an extended period of severe awkwardness until hopefully both of you can get past the giant pink elephant in the room – which may never happen.

OR – Bonus Option #4, you are both superbly enlightened and mature individuals who can get together, have sex, have a relationship, realize it doesn’t work and stay friends just as you were before, maybe even closer friends. Even being able to meet each other’s future girl/boyfriends and be genuinely okay with it. This one is the incredibly rare, practically impossible, almost-never-heard-of option.

friends, lovers, or nothing

The problem lies here: there is no guaranteed way for you to know which one of these outcomes will be your fate. You have to be extremely savvy about the current dynamics of your relationship and try not to judge his reaction based on what you want the outcome to be – but rather, what it will most likely actually be.

The trickiest part of all of this is weighing what the platonic friendship means to you against what it could mean to have a romantic relationship with this guy. From the possible outcomes, the probabilty of it ending up well is only in your favor if you play your cards very carefully, maturely and realistically.

That being said, you only live once and I don’t believe that you’re ever really living if you don’t take chances on love.


If you really feel strongly that you could find love within this friendship, then I wouldn’t turn it down. But be smart about it. Be sure than it isn’t just lust, so if and when you are sure of that – take a chance and tell him how you feel.

If you get married, I want to be invited to the wedding though. That’s my fee for this session. :)

Friends, Lovers or Nothing? Not always.

Love, your friend


Dear Kate is a column that runs on every Thursday at noon. It is written by the wise Katharine Luckinbill, who you should follow on Twitter. Got a life, friendship, family, dating, or relationship question that you’d like Dear Kate to answer? Send it to and she will help you out.

Tagged , , , , ,

One thought on “Dear Kate: I think I’m in love with my best friend. Should I tell him?

  1. omg you TOTALLY can’t go back once you’ve seen each other naked… it’s a fact!

    That being said, I say go for it. I’ve done crazy stupid things and some of them have worked out REALLY well and others not so much. It can be scary and painful and you could potentially lose a friend. There’s a lot at stake. BUT… you can’t help the way you feel and do you really want to spend the rest of your life wondering “what if?”

    If you think there’s a chance he might feel the same way too (and think about that VERY carefully), isn’t it worth it??

Leave a Reply

Your email address will not be published.

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>


Get every new post delivered to your Inbox

Join other followers: