(To target) OMG your friend is so adorable when she's all mad! Aw look at her (pointing and giggling whilst making eye contact with target and kinoing). I can see why you guys get on so well, it's like opposites you know, ying and yang, one of you is always happy and the other is mad. Ok dweedle dum and dweedle dee, so tell me HEY (to obstacle) NO don't smile you're RUINING IT - put on your serious face! [You could transition into Tyler's dressing one of them up as a devil and one as an angel routine if you like that kind of thing from here]
Basically build the connection with the target and make it you two vs the obstacle for a while, whilst being funny and silly about it. Once the obstacle warms up a bit, you could even flip it and spend some time talking to her and say "actually maybe I was wrong, you're actually the fun one!" Making the target jealous and want to prove how she's the fun one
