This question originally appeared on Quora. 
By Phoebe Gavin, Awkward Human, @ohsoordinary
This is all me, all day.
Script Yourself; Direct Conversations
My biggest problem was that I didn't ever know what to talk to people about. Then I realized that there are a few facts about me that are kind of interesting, and if I direct a conversation in that direction, I can control the conversation, but they will still probably enjoy it.
Example:
"So do you have any siblings?"
"Yeah, I have two brothers. You?"
"I have a brother, but my family still feels big. My dad has twenty brothers and sisters."
"WHAT!?"
"Yeah, really! [Story about what it's like to have a bazillion family members]"
"So where did you grow up?"
"Connecticut. Near Stamford. You?"
"Sanibel Island, Florida. You've probably never heard of it."
"Is it a Key?"
"No, it's like right across the state from Miami. [Illustrate location using hand] It's a really small beach town. Kind of old timey. It doesn't have stoplights."
"WHAT!?"
"Yeah, really! [Story about how old timey Sanibel is]"
Think of your factoids and try them on folks. You'll figure out which work and which don't. You'll also notice a trend in the way the conversations go. You'll learn which is the best way to present your factoid and what follow up questions to expect. It's easy to keep the conversation in your wheelhouse as long as you have some good factoids. The other person will be too entertained to realize they haven't said a word.
Smile and Nod
You know what people like more than apple pie, dancing babies, and lolcats? Talking about themselves. So let them. If you know what kind of people you'll interacting with, have some questions queued up. But more importantly have some follow up questions lined up. As long as you keep them talking about themselves, they will think the conversation went GREAT!
Example:
College Students
What school do you go to?
Why did you pick that school?
What is your major?
Why did you pick that major?
What is your coursework like?
What is your campus like?
Is it hard to get around?
Is there are lot of partying?
Do they have fraternities/sororities?
What are the big programs there?
Businessy Folks
What industry/field are you in?
What got you into that industry/field?
What do you like about your industry/field?
What is the new big thing in that industry/field?
What would you change about your industry/field?
What companies are doing great in your industry/field?
What companies are doing poorly in your industry/field?
What did you do for your last vacation?
What is your office like?
Parents
How many kids do you have?
(You don't really need follow up questions. They'll just keep talking)
At some point, you will decide if you want to continue speaking to this person. If you do, just let inertia takeover. The conversation will drift here and there, just let it. That's how you make genuine connections.
Unfortunately, sometimes people are not as exciting or interesting as you would hope. To minimize awkwardness, I try to plan a tactical exit strategy.
Cellphone Timer
When you acquire your social target, set a timer on your phone to go off in five to ten minutes (I go with seven). When it goes off, make a snap decision whether or not you want to remain in the conversation. Yes? Apologize for the interruption, continue talking. No? Apologize, state that the call is from someone important and fake answer it. Walk away. Mom/Dad/Sibling/Roommate is bad. Significant other is good if you want also to quash romantic interest. Spouse/Partner works too. If you also make a fake confused face ("Why are they calling me? This must be important.") it can also be helpful. Boss is the best, accompanied by an annoyed sigh. Makes you look important, but also garners sympathy.
Wingman
If you are with a trustworthy friend who is aware of your... ahem... limitations, have them keep a look out for you and come rescue you if necessary. A signal may help with this. My favorite is eye contact followed by wiping one eye. No wipe, all good. Wipe, rescue me right effing now. Wingman just grabs you and pulls you away. You feign helplessness.
Empty Drink
Social rule #1, always have a drink in your hand. It doesn't have to be alcohol. It just has to be liquid. As you are socializing, navigate away from the drinks source (bar, buffet table, etc.). When your drink is empty, decide whether you want to remain in the conversation. Yes? Ignore the emptiness in your glass - or better - offer to get the person a drink. No? Excuse yourself to the bathroom. Go wash your hands (they have germs on them anyway) then get another drink and find someone else to talk to.
That's my patented, copywritten, but-you-can-still-use-it strategy of minimizing awkwardness.