Dating Over 40: Captivating Conversation – How to Avoid Being Boring

Are you boring?  Who would answer "Yes" to that question? Most people don’t think of themselves as boring and luckily, most people aren’t.  But does that automatically make you intriguing?  Hmmmmm…

When you go out to meet new people, what do you talk about?  Do you discuss work, family,  the weather? How do you feel when someone new starts talking about his/her work -life? Riveted? Spellbound? Captivated?  Probably not.  It’s true, these are the easiest topics and a good way to start a conversation. But will it be memorable or leave a man curious about you, wanting to know more? Not likely.

Boring is often nice, polite, non-descript, bland, everyday, expected, caring and nurturing. Please don’t start taking care of him right from the word go.  Acting like his therapist and care-taking will not get you date number one.

So what’s the solution to mundane conversation?  Don’t talk about mundane topics! Duh right?

When I studied coaching, we were given many exercises to become more curious and ask thought provoking questions. The good news is, anyone can use these techniques.  When you do, you won’t be boring!  Instead you’ll have the possibility of getting into fascinating conversations or drawing someone out to really discover who they are.

There are three different methods and often you might end up using both in one conversation.

#1 – Find out what the other person’s passions are.  For example, ask what was his favorite vacation ever. Or find out about the person’s hobbies.  Maybe he’s involved with a particular cause. When you tap into the passion , the conversation will have enthusiasm and energy and you will see him literally come alive. Often the excitement shared has a contagious affect, causing you both to become animated.

#2 – Really listen to what he is saying and follow the train of thought to get more details.  Ask why he likes Bermuda or soccer, how he got interested, and what future plans he may have about the topic. This is how you start connecting on a deeper level and get past the superficial.

#1 – Know what you are passionate about and have your responses ready.
  When you ask a man questions like this, after a while, the tables might turn and he might ask you the same question.  Be prepared with your own answers so you’re not caught off guard.

#2 – If a man asks how you are, be ready with an unusual response and have a story about something interesting or unusual that just happened to you. Not too long, you have enough details to be understood, but not overwhelm.  Leave something unsaid so he can ask you questions too.

#1 Be playful , use your sense of humor, and verbally tease.
  This can be very exciting and terribly fun. It involves great banter, some social risk taking, feeling confident and leveraging your clever nature.  You might not answer questions directly, add a sly little smile to the end of a sentence, or say things just to get a reaction.  The amount of social risk you take will be up to you.

Overall, the idea is to reach that level of conversation where you are both involved and excited – because this is a way to leave someone wanting to know more.  When you talk about the unexpected, you shake people up and stand apart from the crowd. That’s what makes you memorable and intriguing.  That’s what will make him think about you later, feel curious, and motivated to call – so he can see you again.  

Next time you’re out at a social event – experiment with these techniques.  Don’t wait for the perfect man!  Try this with women, family or any guy at the party or networking event.  See what works for you and how fun it can be! Practice makes you’ll feel a lot more comfortable and capable of taking these social risks once you’ve done it a few times.

Single for too long, Ronnie wanted to find love. She put her skills from personal development and her spiritual path to work, dating 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to manifesting and midlife dating, she founded It’s Never Too Late to help smart, successful women find love or live an empowered and magical life. Ronnie Ann Ryan, MBA, CCC, is a Certified Coach who has helped 1,000s of midlife women with her Love & Magical Life Coach services. She’s the host of the Breathe Love & Magic podcast and has been featured on NBC, ABC, & Fox News, NPR, BBC, eHarmony,, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

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