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Networking Blunders Entrepreneurs share their most awkward networking moments.

By James Park

Opinions expressed by Entrepreneur contributors are their own.

Networking is hard. It's not easy going up to somebody you don't know, or barely know, under the guise of being interested when all you really want to do is make a sale.

So we can sympathize with Robert Smith when he remembers running into Craig Williams, a contestant in the third season of NBC's The Apprentice, outside a hotel in Atlanta last year. Smith, 32, who owns his own PR firm, Robert Smith & Associates PR, thought he saw a golden opportunity when he ran into the pseudocelebrity. And he promptly wasted it by rambling about Donald Trump. "Not 'Hi, how are you?'" Smith recalls regretfully. "I just said, 'What is it like working with Donald Trump?'"

Of course, in networking, when you see an opportunity, you should take it. But a funeral is not an opportunity. Andy Abend, 36, co-founder of the Abend & Moore advertising firm in Atlanta, was attending a memorial service with his business partner, Tom Moore, 41, last year when several people approached them asking to do business. "We were very taken aback," Abend says. "We said, 'Now is not the time. If you want to talk, give us a call,' which no one has. And that makes it even more awkward."

Stephanie Jo Klein, 29, knows awkward. Last year, the owner of Klein Creative Communications, a marketing firm with a focus on product placement in gift bags, was on the phone with a pushy service provider who had ideas not only for her business, but also for her romantic life. After telling her how she should run her company, he asked if she was single and patched another person into the call. Needless to say, that didn't go anywhere.

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