Do you prefer big crowds or small groups?
While rap songs encourage you to "roll deep" i.e. - show up with a lot of people, I find large groups really difficult to manage. You'll be at one bar, getting ready to go to the next, and someone will say "Just let me finish this drink..." which is REASONABLE and UNDERSTANDABLE, but then other people will think "Oh, I can get another drink..." and then 45 minutes later you'll have to forcibly stand up and say "I'M GOING TO THE NEXT BAR." or else you'll be there for another 45 minutes.
So...yes. Small groups are a little better. Also: you look less intimidating!