How do you build trust for someone who’s done wrong things in their past?

princess23 asks: I saw that boy I like last week, and our mutual best friend told me that he said I looked really pretty, and she told me that every time he sees me he tells her the same thing. I used to see him like a crush, but now I think I’m really starting to like him. Sometimes I feel like I should tell him I’m starting to have feelings for him, but I’m scared that he’ll say he can’t be with me, cause he just got out of a relationship that was kinda complicated! I feel that I have to get over him and not show interest, but he can say all the right things at the right moment. I know that maybe he isn’t the guy for me (or maybe he is) but he has done things wrong in his past and I’m afraid he’ll do them to me. Is it normal to feel this way? I don’t know what to do, I’m super confused please help me!

Hi princess23 –



You’re right you’re super-confused.  You’re so confused you’ve got ME all confused now!


So if I have this straight, you like this boy and are getting to like him more; you know he’s at least very attracted to you, and willing to tell your friend about it; and the main reason you don’t want to approach him is that his last relationship was “kinda complicated” and he did some wrong things.


Is all that correct?


If so, what you’re really dealing with is two issues.  First, the usual shyness that comes with being attracted to someone.   For those, I have a bunch of posts on the AskShirelle website.  Just use the Search box and type in words like “shy, crush, like, love” and you’ll get a bunch.


But then we get to the “complicated” part.  Now when you say he did some wrong things, do you mean that he’s gotten in trouble at school, maybe got caught drinking or smoking something, or called someone a name?  Or is it that he got angry at his last girlfriend, that he cheated on her, that he hit her?


You see, what you’re really dealing with is the question of, if you did go out with this boy, how you could trust him.  Dating without trust simply stinks, so you don’t want to get into that mess.  So you would want to be able to talk with him about whatever it is that’s bothering you, and see how he talks about it.


And then, you would have to make some very difficult decisions.


Let’s say, for example that he got a tattoo a year ago, and you just hate tattoos.  You might want to get him to promise that he won’t get another one as long as you two are dating, but deal with the one that’s already there.


Now, let’s say he cheated on his last girlfriend.  That might be a lot harder to trust him about.  Maybe you could let him know that there’s a “no tolerance” policy here – that if he has any romance with another girl, you’re out the door.  But still, you’ll have to deal with your own fears and suspicions of what he’s not telling you.


Now then, let’s say he hit her.  That’s a really difficult one.  Because, although you can create a similar “no tolerance” statement to him, you will still always be frightened, if you two have an argument, that he might break and do it again.  So you might choose, instead, to say that you’ll never date a guy who’s done that – and because of that, yes, have to get over him.


So here’s what all this is adding up to, prettyndsweet12.  Unless he did something that you absolutely can’t tolerate, it sounds like you two are pretty into each other, and might as well at least try to meet up.  But I think you need to talk about these “complications.”  You need to, before you talk with him, clarify in your own head what boundaries you have, and when you talk with him, state them very very clearly.  You might even write them down.  “If I’m going to go on even one date with you, you have to promise me you won’t have another cigarette as long as we’re together.”  Whatever it is.


Now if he’s as good a guy as I’m hoping, he might work to negotiate with you.  “How about I never have a cigarette with you, and if I start to get addicted to them, I’ll quit?”  What I like about him negotiating is that it makes me think he’s committing to honesty, instead of just agreeing with whatever you say, which means he might well sneak around and disobey you.


So here we’ve talked about bad stuff so much that we’re taking the fun out of the fact:  Hey princess23, you’re excited about a boy who’s really into you!  That’s a great thing!  It doesn’t happen enough!  No matter what happens, this is fantastic news!!!





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