I dine at a local restaurant where I often see a man who usually eats alone. How can I ask him if he wants to join me for dinner?

Make an effort to be seated near the person dining alone, and when he looks in your direction, make eye contact, nod, and smile. If he smiles back, you can say, "Hello. I've noticed that you eat here a lot, too. What's for dinner tonight?" Remember that you are just showing interest and seeing if he appears open for contact. If his response is friendly, you might say, "I really like their sandwiches here, but tonight I feel like something different. What do you usually order?" The goal is to start a conversation from your separate seats and see where it leads. If it seems like he wants to continue to talk you can say, "If you're not waiting for someone, would you like to join me?" or "Do you mind if I join you?"

Many people who frequently dine alone might be happy to accept your invitation if you approach them in a friendly and low-pressured way. You can also offer to buy a person a drink to show you are interested in chatting with him. Just remember that your offer is only a friendly gesture and doesn't necessarily mean that you are treating him to dinner or that he owes you anything in return. However, if he declines your invitation, he may be shy or he might simply prefer his own company. Don't get upset or angry. Just smile and say, "No problem, enjoy your meal."

The Perfect Time to Introduce Yourself

Exchanging ritual information also allows you to prepare to introduce yourself to the other person. Generally, the longer you wait to make an introduction, the more uncomfortable people get, so the sooner you take the initiative, the better. When there is a pause in conversation, this as good time to say, "By the way, my name is. . . What's your?" The other person will almost certainly respond in kind. Offer a handshake and a friendly smile, and say: "Nice to meet you."  Then as a question or make a comment about what the other person has told you, and your conversation will be off and running.

 Click Here Small Talk With a Man.  The Right Thing to Say at The Right Time Part 5.

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