How to tell someone you’re interested in them

PERFECTION asks: I want to tell someone how I really feel, and I just want to make it honest and sincere but the only thing that I’m worried about is that I don’t know how to do it, any tips?



I’m never one to call my Pack members liars, but I’m going to break that rule and call you out, my friend:  HOOEY!  PURE HOOEY!  PURE LITTERBOX MATERIAL!!!


Not that you don’t like that person, or have strong feelings for them; I’m sure that’s true.  What I’m calling you out on is when you say you “just want to make it honest and sincere,” but “don’t know how to do it.”  What a load of kitty poop!


Of course you know how to tell them your feelings with honesty and sincerity.  What you don’t  know is how to do it in a way you’re sure they’ll like!  THAT’S what you’re worried about, and that makes complete sense!


And I’m glad to try to help.


And I really do mean “try,” because of course you and I are very different.  But my experience might be instructive.  (Oooh doesn’t that sound adult!)


I have always, all my life, liked people and dogs on sight, and wanted to play with them.  When I was a young puppy, I attempted to do this by doing just what came naturally to me – walking up to them and biting them.  My brothers and sisters played with me when I did that to them… but strangely, it really seemed to bother most humans and grown-up pooches.  Especially if I did it when they weren’t expecting it.  I got barked at, bit, and yelled at a lot.


And slowly I learned.  Even though my honest, sincere, expression was to bite them, they liked  it better if I did other things.  Like walked up and licked them.  Or brought them a toy to play with.  Or just sat and let them pet me.  Or, with dogs, caught their eye and ran away so they’d chase me.  And these techniques worked, and work to this day.


Of course, though, you’re in a more complex situation.  You want to tell  someone something intimate and meaningful.  And it will mean a lot to you if they like it and accept it, or dislike it and reject it.  So what can you do to improve your chances of it being a happy conversation?  Here are a few suggestions.


  • Don’t be scary. Just as people are frightened when a dog runs at them with teeth bared, they’re also put off when someone’s energy is too forceful and needy.  “I LOVE YOU AND CAN’T LIVE ANOTHER DAY WITHOUT YOU AGREEING TO MARRY ME AND HAVE GRANDCHILDREN WITH ME” is not likely to work; “So, I’ve really enjoyed talking with you.  I’d love to hang out sometime.  Would you like that?”  Oooh, that sounds WAY smoother!
  • Keep it between you two. Although you might feel ‘safety in numbers,’ it puts the other person in a really rough position if you start saying these things when other friends are around.  Those stories we hear about people proposing on TV broadcasts or with airplane skywriting?  That can be a great idea if you’re absolutely sure they want to say yes; otherwise it’s a recipe for horrible humiliation for everyone involved.
  • Have you ever heard the anagram K.I.S.S.? “Keep It Simple, Stupid?”  As complicated as your feelings might seem to you, they’re actually pretty simple.  “I really like you a lot.”  “I’m falling in love with you.”  See how quick those are?  An old friend of mine was visiting, and told Handsome and me a story just this week, where a just-friend nervously gave her a long speech telling her he wanted to be more than friends, but his nervousness and confused talk actually made her think he was saying he wasn’t  interested in her!   They then had to have another conversation to clarify that he was!  (It worked out, though – they’re married and have two beautiful children now!)
  • Make any consequences clear. Are you saying to this person “I feel this way about you, and there’s nothing you need to do about it; I’ll be your friend either way?”  Or “I can’t take just being friends anymore, and if you aren’t willing to become more than that, I’m going to have to spend less time with you – or even cut you out of my life completely?”  I’m not saying that one’s right and one’s wrong; I just want you to be fully honest about this part too – in a way that THEY UNDERSTAND.
  • And last but not least, be kind. I know, it feels like you’re the one in the difficult position, but so are they.  Make it as easy as you can.  Speak softly, give them compliments (real ones, not fake), maybe even apologize at first, “I’m sorry if this makes you uncomfortable, but there’s something I really have to talk about with you.”


There’s never any way of knowing how these conversations will work out.  But if you do these behaviors, I do think I can guarantee it’ll work out as well as possible for both of you, regardless of what interest they express or don’t.


But you KNOW I’m cheering you on!  LET THEM SEE YOUR HEART as you’ve let me see it, and I’m thinking you’ll do great.


Best of Luck!


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