How to get someone who likes you to ask you out

Mandhie asks: Recently, this guy and I had been chatting on whatsapp and he asked me a question that made me feel uncomfortable. We had a conversation one day and I was like “I miss you” playfully, and he replied “lol… really?” which made me feel like I was pushing him to say he misses me too. So I sent a sad emoticon and he asked “r u sad?” I replied… “of course. I am saying I miss you and you asked am I sure?” And then he sent the love emoticon and wrote, “Okay I love you and I miss you too” and our chat continued. Then, recently, I had a message from him, asking me, “What do you feel about the ‘I love you’ I sent?” I replied to him, “You were saying it on friendly terms.” (Shirelle, remember, he is not my boyfriend yet so we are taking our time to get closer. I didn’t want him to feel I took the “I love you” personally, which was the reason I told him it was said on friendly terms.) So now, here is my question… the way we are now, I won’t be surprised if, in the next two years, we go out. We have grown so close, and the teasing from our families and friends has been increasing. If the “I love you” wasn’t just on friendly terms to make me feel happy when I told him I was sad, why is he taking too long to ask me out? Because I really feel this time he likes me. Oh, and his best friend told me, “he likes you more than you like him… trust me.” So you see, please, I really need to know! What is keeping him from asking me out? 🙁

Hi Mandhie –

I’m a little confused here.  On one hand, you’re telling me that, if things keep going the way they are, you and he will be going out in two years.  Then you ask why he’s taking so long to ask you out.  In fact, it’s pretty clear his not asking you out is driving you nuts!

It sounds to me like you’re dealing with a boy who’s not quite as ready as you.  That doesn’t mean he’s not interested; it just means he’s not ready for the risk.

Which brings up the question: What Risks?!  Well, I don’t know the boy at all, but I can imagine a few.  For example:

–       What if you say no?  You’re saying you miss him, but that’s not the same as going out.

–       What if there’s some pressure on him not to date too young?

–       What if he doesn’t have the money to take you out?

–       What if he’s not sure what he’d do with you if you went on a date?  Especially with all the stuff everyone’s saying to you two, he might feel very pressured to do something with you, and report it back to them.

–       And speaking of that pressure, what if all those teasing comments make him feel like he’s being pushed into taking you out?  You two are at the age where it’s very normal to want very badly to define yourself, and not be the way others want you to be (as was normal when you were younger children).  Maybe he wants to make sure that what happens between the two of you is yours alone, and not just fitting in with what others think should be.

Now again, I don’t know the boy.  But you do.

So is there something you could do to help this along?  What if, for example, you asked him something like, “If we were ever going to go out on a date, where would you want to go?  What would you want to do?”  And maybe he’d get excited by that, or maybe he’d pull back in fear.  And either one would tell you a lot about where he is.

And maybe you could kind of prod him along.  So if he says he’d want to go to a beach, maybe you could say “Oh I’d love that.  We should sometime!”  And if he says, “Oh I don’t know, I don’t think about things like that,” then you could say, “Really?  Oh I do.  I think I’d like to go to that cool new restaurant.  Do you know about it?”  And let things proceed from there.

Again, Mandhie, it really sounds like this isn’t about him not being interested in you; it’s just that something is keeping him from taking you out.  And the sooner you can figure out what that is, the better chance there is that you can get this party started!

Good Luck!


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