How can I make him really see his self worth??

So I've found myself in an incredibly weird situation relationship wise- I identified as lesbian for the last several years having two semi serious relationships with girls. Until about six months ago I fell for a guy. Mixed emotions and I was confused but came to terms with the fact that I was bi and decided to forget labels and fall for who I fell for.

He was 29 and I was 17 so I knew nothing would come of it and accepted that. But then he began helping me with school and such when he found out I was recovering from depression and bulimia.He went overseas with work for three months and we talked every day at least once. We became really good friends and when he was back in the country we both found out the we had feelings for each other and despite him moving away in four months time we started seeing each other secretly- the drama of other people knowing would not be worth it given we are essentially dating with a deadline.

Its two months till he goes and we both aren't looking forward to when he leaves.

He dated a girl for four years, three years ago they broke up. He's now about to reach thirty and I can tell that a deep insecurity for him (we've talked about it a wee bit) is that he will never find someone seeing as everyone he knows seems to have met the person they are marrying now in the period he was dating/getting over his ex.

I can tell it really gets to him and he is often very insecure in himself in terms of his appearance and personality and I know this is a huge factor into why he hasn't met someone else. I want to be able to make him feel more self worth and understand how much of a great person he is. He is the sweetest and most genuinely caring guy I know and it kills me that he can't see that and even though he knows he's the nice guy he sees that as a negative because people sometimes use him..

What can I do to make him more confident in himself? I know constantly reassuring him when he makes comments about himself can work but I know too much of that can have the opposite effect where he'd be relying on me for self esteem..

Sorry its longbut thank you for answering!

 

Anyone?? This guy is the nicest guy I've met and I wish he could see how amazing every aspect of him is but I'm just not someone whos ever been good at words