1) At first it's awkward between us but within 5 minutes we start making bad jokes.
2) Things are awkward at the beginning but in just 5 minutes we start cracking bad jokes.
1) & 2) "初めはぎこちなくとも五分もすれば悪い冗談始まってる"
初めはぎこちなく : At first it's awkward between us / Things are awkward at the beginning.
何分かしたら : within 5 minutes / in just 5 minutes.
悪い冗談始まってる (私たちは悪い冗談をつくりはじめる) : we start making bad jokes / we start cracking bad jokes.