How to ask someone to be your boyfriend or girlfriend

Outcast asks: I chickened out on asking the girl I like to be my girlfriend. I don’t know what’s wrong with me. I just need an idea on how to tell her. Do you have any idea I can use?

Hi Outcast –



I hardly ever disagree with things people say when they ask me questions, but in your case I’m inclined to.  You say you “chickened out,” and that there’s something wrong with you.  But from what you’ve written me before, it sounds like there were lots of reasons to suspect that she’s not ready for a relationship yet, and would reject you.


Now yes, I did encourage you to go ahead and try if you wanted to.  And I would have loved you doing that.  But as it is, I wonder if you actually had a smarter voice than me, that little voice inside your head, that read her correctly.  And said “Don’t do it, Outcast.  At least, don’t do it now.  Let her grow, and let your relationship grow.  And see where that goes.”


I’m a big fan of instinct, and live much of my life by trusting mine.  And I find one huge mistake humans make is to not listen to theirs, and instead trust some idea they’ve been told.


So I’m not going to call you chicken, or say something’s wrong with you.  Instead, I’m going to say you are smart, instinctual, and sensitive to her feelings.


But NOW, with all that going for you, what can we do to win her over?!


Well, you’ve told me she’s been hurt before in a relationship.  One easy thing is to get her talking about it.  What was bad about it?  How did she get hurt?  As specific as possible!


Did someone cheat on her?  Did someone shame her?  Did someone hit  her?!


Well the more she gets to know you, the more she’ll see that you’re not a cheat, a shamer, a beater.  So that’s a great way to start trust.


Then maybe you could tell her about something similar you went through.  Maybe you’ve never been cheated on but you have another friend who was, and seeing that really taught you how awful cheating is.  And your saying this will build her trust more.


But while you’re working to be her trustworthy friend, you also want to be what she hasn’t had since that last relationship – the most fun thing in her life.  Can you two go to a movie together (if that sounds like too much of a “date,” maybe you could do it with some other friends along)?  An amusement park? A hike?


And when you do, can you be funny, bright, charming?  Can you share your favorite music?  Can you tell your favorite jokes and make fun of something she’s wearing (but in a way she’d enjoy)?  Can you grab a stick and drop it in her lap and run circles around her and jump up and down for it and… oh wait, that’s what I’d do.  But you get the idea, right?


If you can be the person she trusts most, and the most fun thing in her life, that will put you in great shape to get her interested, and eventually to dare those questions you “chickened out” on before.


And my guess is that you will prove that you weren’t a chicken at all, but the cleverest bird in the flock.




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