After you're comfortable going to a bar during the non-busy times, try going during happy hour. Arrive at the beginning so it won't be as crowded and you'll have your pick of barstools. And because you already know the bartender, you'll have something to talk about when you sit down. The next step will be to say hello to (or at least smile at) anyone who sits near you.
You might be thinking, "Oh no, what will I talk about?"
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I had to address this in my single days as well. Even though I'm someone who's comfortable talking to anyone at any time about anything—I knew I could get flustered if I met someone who looked interesting, so I would come prepared with possible subjects. My preparations included:
- Paying attention to the news that day.
- Consulting my "reference book"—The Complete Book of Questions: 1001 Conversation Starters for Any Occasion.
- Figuring out 5-10 topics and questions from the above resources and writing them down in the small notebook I used as my "cheat sheet." If I got stuck for something to say, I'd open my purse "to get out a Kleenex or lipstick" and pick out the next item.
To give yourself a little jump start, you might enjoy seeing the movie He's Just Not That Into You. The main male character owns a bar and watching him will give you a sense of how to talk to bartenders.
In closing, I'd like to give you one more bartender tip. The local bartenders you befriend will know (without asking) how to serve your drinks. If you don't drink alcohol, they'll be happy to make you a non-alcoholic drink, and you can ask for it in any type of glass you wish (my friend used to drink flavored, no bubbles water out of a martini glass). If you do drink alcohol, then to ensure you don't become inebriated (a concern of mine because I'm a light-weight) you can pre-arrange with the bartender to water down your wine with an ice cube or to use less alcohol in your mixed drinks. When you start talking to that man sitting next to you and he offers to buy you a drink, the bartender will already know how to serve you.
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So, give it a try. Visit a few bars. Have conversations with several different bartenders. With each success, your confidence will grow. Before you know it, you'll be taking these skills to other events and you'll find yourself easily chatting with everyone there.