The Sea: How I Met Your Brother (2015)

Three Unlikely roommates must learn to live together while navigating the sea of online dating. Jack breaks into his estranged Sisters apartment after he is robbed blind by an internet hooker on 'tender', an online dating app. When they end up contacting the police Jack is the one who could get in trouble and it's up to his sister Samantha and her roommate to lookout for him or send him packing onto the street.