This might sound like your typical male answer but many female friends of mine told me it is the best and most efficient way – and I am not talking about honesty!

You must create a situation where you both are little drunk, this way you (and him) will overcome you shyness. You said your roommates are friends with him – so try to throw a party or something of this sort, have a few drinks have a couple of tense free laughs and go with the flow!