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Conversation openers that work. How to start a conversation with a man. Avoid asking, “What do you do?” 

By Tom P Blake - Finding Love after 50

You would not think that the words, "Is that yours, dirt bag?" was a one of the most successful conversation openers ever. Believe it or not, that conversation opener worked.


Meeting potential mates is difficult for mature singles. When an opportunity to meet someone presents itself, it's likely a one-time occurrence. Seldom do singles encounter the same stranger a second time, so they need to be assertive at that very moment to improve their chances of establishing a relationship


This applies to women as well as men. But some women are shy and others are at a loss about how to start a conversation with a man.


Janet wrote, "I was wondering if you could run a column about appropriate "pick up" lines for older people? I ask because my sister insists on asking new men she meets 'What do you do?' 


"Her reason for asking this, according to her, is to have a basis of conversation. I think it's because she is screening them, i.e., if the man answers 'truck driver,' she will probably limit her time speaking with him. However, if he answers 'attorney,' this will perk her interest."

Janet feels her sister's question, "What do you do?" is a turn-off to men. "Good men rule her out because they think she is only interested in how prestigious their careers are or how much money they make. Would some men find my sister's opening line slightly offensive, or at the least, nosey?" Janet asked.


In the world of mid-life dating, we don't call them "pickup lines" anymore; that was in the old days when we were camped on barstools trying to hit on the opposite sex. "Ice breakers" or "conversation openers" are better suited descriptions.


Most men would find the "What do you do?" question offensive for the reasons Janet described. A former neighbor of mine, Larry, now single, says in Newport Beach (California), where he hangs out these days, what a man does and earns is at the top of the list of qualities single women seek and they waste no time popping the "What do you do?" question. 


Larry is a devilish guy with a twinkle in his eye. Sometimes he'll answer, "I inherited a large sum of money and investing it is a full-time job so I don't work." Larry says that that comment piques their interest.


Another long-time friend, Bob, Laguna Beach, a few miles down the road from Newport Beach, says that "Where were you born?" is a more effective conversation starter. "It shows a personal interest and is a little different and catches someone off guard. But, the answer is easy, making it possible to explore things not so automatic or time worn.


"A chance encounter hit pay dirt for me when a woman's home town in the Midwest matched mine. She attended a school located on the street where I was born."


Carlene told us a month ago how she met a man wearing a kilt while standing in the food line at an outdoor Scottish Festival: "First a big smile and genuine hello followed by, 'What would you suggest from the menu?'"


Then, the quick-thinking Carlene followed with "I like your kilt." That led to romance and a relationship with him. "Once you show you are friendly and open, it's easier to meet someone," Carlene said.


Bob added that any first question with tasteful humor attached will open doors, as happened to him in the check-out line at Costco. A man behind Bob had a bag of fertilized soil in his shopping cart. A woman in the same line gave Bob a "broad, lovely smile" and said, "Is that yours, dirt bag?"  


Bob said, "We both walked out to our cars lighter, and a bit fascinated how a smile fits perfectly into those new moments of an encounter. Even when the words come out all tumbled together."


The most important aspect of a conversation opener for older singles is being friendly. It's not so much what you say but how you say it. As long as you don't say, "What do you do?" Of course, saying nothing gets you nowhere.


Plus, be careful how you use the "dirt bag" line. Some recipients might not be as affable as Bob. And remember, that smile does wonders.

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