Honestly, when I gamble with my friends, I feel there's no pressure, but purely as entertainment. We collect money, and deposit it to one of our 2 favorite crypto casinos (Rollbit & Stake.com), sometimes it's in his account and sometimes it's in mine, we share the bankroll and play it with full fun. When playing alone and losing $100, it's harder than knowing that you only lost $50 and the other $50 came from your friend money.