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Ask his server what he's drinking, and ask them to bring him one from you.I tried this once, simply as a social experiment, and it was both hilarious and successful. After I sent him the beer, he, of course, came up to my table and said thank you, and he even sat down at my table for a bit. You can also check for cute guys holding almost-empty beers and say, “I'm going to grab myself a beer. ”Always go to parties with your outgoing friends because if all else fails, you can get them to march right up to the guy you want to talk to and say, “Hey, I want you to meet my friend!
If you're at Starbucks, for example, try tapping him on the shoulder and saying something like, “Hey, if I buy a brownie will you eat half? And the type of guy you'll meet while volunteering will probably be a good-quality, nice guy you can bring home to Mom.
If you're in the same volunteering group, you can chat with him, mention you're going to be volunteering at another event next weekend and ask him if he'd like to join you.
Even if you're cheering for opposing teams, you can joke around with each other about it, aka you can flirt with each other.
Whether you're waiting to board the same flight at the airport or in the waiting room at the dentist's office, you have an excuse to chat with someone when there's time to kill.
Plenty of successful, entrepreneurial men work all day or all night at coffee shops.