Dating Guru’s Mailbag – I can’t work him out!

Here is another dating problem

for our Dating Expert


Hi James,

I’m very confused so please can you help? It all began when we were introduced via facebook through my brother. I messaged him first and he texted back with lots of smileys and with very bubbly enthusiasm. He seemed more than excited to meet up. However when we did meet he couldn’t even look or speak to me. He’d only reply briefly to a question I’d ask every now and then. Then later on as the days went by and we met up more frequently he became more relaxed and was able to look at me and initiate brief convo. Later he’d always go to his room and he’d stay there like he always usually does, away from the rest of us in his own little world.

(a brief note: his 3 siblings have told me how he was always the shy quiet child playing alone when they were kids. They said he had a shell and it needed time to break down. And he’s only ever had 1 girlfriend his entire life, that too was because the girl begged him, they say)

So then he left back to his home town and I tried to occasionally keep in touch through fb. He’d be nice with smiley faces and a few sentences, but whenever I felt he was comfortable enough with me and I tried asking simple things to get to know him as a person like hobbies and things, he wouldn’t reply and he’d just ignore my messages. I thought to myself, ‘I’m always the one initiating and no matter what I do, he won’t open up. I give up. He’s not interested’. Then just a week ago I saw him online on fb and I said hi. He was happy to hear from me (as always when he talks) and asked me many questions about my uni. He made the effort to keep the conversation going and then left again..

Basically, I don’t know what’s going on. A big part of me tells me he’s not interested. but if that’s the case, why does he even bother having a conversation anyway?  PLEASE tell me what on earth is going on inside his head???”


It does certainly sound like he is giving you very conflicting messages, so it’s no wonder you are confused.

There are two possibilities here:

1) He is indeed very shy and likes you.  The fact he couldn’t look you in eye and is asking all these questions now indicates this. Usually these types of people are shy because they have been hurt in the past so will act strangely to protect themselves. If he’s worth it then you should work towards breaking down his barriers.

2) He’s not interested but doesn’t know how to let you know.  Sometimes men string women along just to avoid hurting their feelings OR as an ego boost they don’t want to lose.

Either way, he’s not being fair to you and he needs to stop playing games with your emotions.

You’ve not said anything why you like him.  What do you have in common?  Are you genuinely interested in dating him or has he become such a challenge that you want to work out the mystery?

The only way you are ever going to really know what is going on is to gently confront him about his behavior. Do this face to face rather than by Facebook. Tell him you like him and would love to know what where you stand.  Don’t be too demanding or he won’t be honest.

If he doesn’t offer any kind of answer to you then it’s time to just delete him from your friends list and move on. Spend your time getting to know someone else who is ready to make time for you and deserves you.

I hope everything works out well for you.

James Preece

The Dating Guru

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