Here’s some quick tips to make the intimidating challenge of going out to bars fun (isn’t it just sad that we as a society have devolved to where we need to remind each other how to have fun when we go out to have fun?) 
Follow a warmup routine. Find music that puts you in a good mood, or a comedy CD. I like to have the same CDs on rotation in my car (Tupac, Afghan Whigs, Supersuckers, depending on the bar), and tell myself bits from Chris Rock, Dave Attell, etc, to get myself happy and upbeat. The better your mood going in, the easier it is to positively afffect the mood of others.
On your way in, start talking to everyone. Stop every group you walk by and ask them for directions to the place you are going (yes, especially if you already know where it is). This will get you out of your head, and get you talking to strangers. It’s ok to talk to your wings, but better to talk to others.
Talk to the doorman and bartenders when you get in. Simple social stuff. Ask them how the place is tonight. Introduce yourself. Smile and be friendly. I worked the door and the bar for years, so I know from experience… they are bored out of their minds, and probably annoyed dealing with drunks who either try to act too cool for school
or ignore them entirely. You’d be amazed how friendly they will be if you just start with “Hi, I’m Chris,” and shake their hand.
Now that you’ve started chatting people on the way in, find the first happy-looking group you can spot, walk up to them, and say “what’s up. you guys having a good time tonight?” Smile and let them answer. Talk to them like a friendly stranger (which is what you are). Do NOT run game on them… you just want standard social stuff so you get talking. Talk for just a few seconds and excuse yourself by saying something like “Cool meeting you guys. Later.”
Once you’ve done all of this, you will now be in a place where you feel comfortable and social, as opposed to the groups of guys who walk in, heads down, grab a beer and pin themselves to the wall and talk only to each other. And others in the bar will likely notice that you are smiling, talking, and friendly, and be pre-disposed to talk to you when you approach.
Sean
