Ask Sam letter


To Sam

Ahh I really like a boy,

Hi Sam,

Me and my friend really like this boy. But the thing is we both think he's going out with our worst enemy. I feel really sad and it's actually getting me down.

I keep on thinking about them and they always talk on Instagram and post pictures of each other. I'm really sad. I want to ask him out but I just don't have the confidence.

How do you ask a boy out? I attempted talking on 1-2-1 but I got really scared and I couldn't. So in a way this is my last shot. I can't ask my Mum for advice either cause I get so embarrassed.

Please please reply. I need some help. Oh and also I looked online and there was nothing at all. He likes really confident girls. I'm the total opposite.

Yours faithfully,


Ask Sam


Hi C*

Thanks for your message. I’m really glad you felt you could contact me to talk about how you feel, well done for having the courage to get in touch. 

I can hear how much you like this boy and how down you feel when you think about him going out with your enemy. It can be really hard if you like someone a lot but don’t know if they feel the same.

Just so you know it’s totally normal to feel shy about asking someone out. Taking a risk and telling someone how you feel about them can be really scary, even for the most outgoing people. If you’re feeling embarrassed and low in confidence perhaps it may help to build your confidence up first, before thinking of asking him out. There is some great advice about boosting your confidence in the explore section.

You say this guy likes really confident girls, but if that’s not who you want to be, you shouldn’t feel you have to change for his sake. It’s always worth doing things to feel more confident but it’s best to do it for yourself, rather than for other people. There can be many reasons for not feeling confident and perhaps when you feel ready you can try talking to a ChildLine counsellor about it.

If you think this boy is going out with someone already (your enemy) then it might be best to wait to see if they break up before you ask him out. Going after other people’s boyfriends is not respectful and I’d be worried that it could create more problems for you. I know it can be hard when someone is on your mind all the time.

You don’t say how you know this boy. When you really like someone, jumping straight into asking them out can seem like a huge step. Some people find it helps to start by just spending time with the person they like first. Try and see if you can become friends. When you feel ready to take it further, some people ask the person out on a date or just to hang out, like going to the cinema or going into town. If you are thinking about asking someone out, it might help to look at the message boards to see what other young people suggest you should do or say.

I encourage you to talk some more with ChildLine, maybe you can try writing an email first? Some people start with emailing before trying a 1-2-1 chat. You might find that the more you do it, the more confident you get with talking about how you feel.

Hope this helps and good luck


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