Sam had and always is accepting of the LGBTQ+ so when Sam found out that Dean was one of them, Sammy was ecstatic. Of course Dean didn’t know that Sam knew, but Sam saw the Bisexual flag hung up on Deans wall one day when he went in to grab a par of boxers, and jeans. So now Sam was trying to get it out of Dean without making it to obvious. “Hey Dean, you need to talk about anything? Ya know get something off your chest?”