Dating Over 40: Some Dating Advice for Men (and Women) – The Art of Small Talk

This weekend I met with a new male client who is 47, wants to find a woman, get married and have children. He’s an average looking guy, personable enough, has a good job, owns his own home. What’s the hitch?


Recently Joe tried speed dating and chose two women, but they didn’t choose him back. That happens all the time, but I asked, "What did you talk about in those eight minutes?"


He explained how he only used his half of the eight minutes to tell the women him about himself, his job, etc. Then he asked his speed dates to talk about themselves. My jaw dropped. I said "Joe, you can’t do that. That’s not a conversation. That’s called ‘Running your Resume’ and women don’t like it. Instead, the best thing you can do is ask the woman a question and focus the conversation on getting to know her." Joe responded with quite a bit of anger, "I’m not interested in small talk!" Huh? That’s ridiculous.


I explained to Joe that dating is a game with some pretty specific rules and if he doesn’t want to play, he probably won’t win. I don’t mean a game of manipulation or dishonestly. Getting to know someone requires give and take and so does conversation. You have to start somewhere. And spitting out a bunch of factoids is not a conversation.


I told Joe that women want to know he’s interested and asking her questions demonstrates this. He’ll get plenty of points which will give him an advantage over probably 75% of the other single men.


He literally waved me off with his hand, making it perfectly clear he wasn’t going to do any such thing. Yet, his very next question was laced with frustration because he doesn’t understand why people don’t ask him questions. For example, he asks his colleagues at work about themselves, their kids, their hobbies, but no one ever asks him anything about himself.


I smiled. "Joe, may be you volunteer too much unsolicited information" Think of this exchange like a business networking meeting. Proper etiquette requires that you don’t give your card to someone who doesn’t ask for it. You ask for theirs, then hope they ask for yours in return. Many people today don’t follow this guideline, but that’s how it’s supposed to work.


When he starts rattling off details about himself, Joe probably offers too much and doesn’t stop to think if the other person even cares. They get more details then they want – what’s left to ask?


Finally, Joe paused to think. It sure looked like an ah-ha moment.


There’s no getting around the small talk of dating, just like there’s no way to directly meet your wife/husband. Dating is a process and skipping steps is very unlikely.  Engaging in small talk improves your conversation skills and allows you to get comfortable with talking to strangers. If you feel like Joe and want to avoid talking to new people, you are missing a valuable opportunity to meet and connect with new prospects.


Whether you’re a woman or a man, when you meet someone new, get curious about them. The more people you talk to people, the more comfortable you’ll become, which builds confidence and your attractiveness. It’s a fabulous chain reaction! Begin to enjoy and excel at this process and your romantic life will flourish. So will the rest of your life as well.


Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony,,, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

Leave a Comment