Bored woman in coffee house with male friendHave you ever been on a first date with someone who droned on and on about a topic of absolutely no interest to you? You know the kind of date where you found¬†yourself nodding up and down like a bobble-head, hoping that he‚Äôd just stop talking, praying for the date to end?¬†First dates can be a crap shoot, especially if you meet online. He’s¬†charming on the phone, but in person there is no connection. What do you do when your¬†date bores you to tears?

Cindy and Darren – a love story?

My client Cindy met Darren¬†online. She’s in her late fifties and looks at least ten years younger. Vibrant, funny, pretty, and smart, she has no trouble attracting men. Her problem is finding a man she likes¬†– someone who’s smart and fun to be with, kind, and generous in spirit.

She spotted Darren’s well-written profile and very handsome photos on She was excited to learn more about him. I helped her initiate contact by writing an email that spoke to their shared love of the Grateful Dead and travel to Israel and Africa.

He wrote back right away, equally impressed with her profile, and they spoke by phone the next day. They arranged to meet the following night for dinner. So far so good. Many men take weeks to get to that first date. He gets bonus points for quickly escalating the communication from first email to first phone call to first date.

And then they met…

The following evening, Cindy showed up to the restaurant on time. She waited for Darren. And waited. And waited. She began to get annoyed. Why didn’t he text or call? So, she texted him. He texted back that¬†he’d be there soon and would explain when he saw her. He¬†said he had a good excuse. He told her¬†it was a long story, and he‚Äôd explain when he got there.

Accountability is very important to Cindy. It’s one of her must-haves in a relationship. But because this was a first date and she didn’t yet know why Darren¬†was late, she wanted to give him the benefit of the doubt. What if someone in his family was sick? What if he had a car¬†accident? She was open to hearing¬†why he was delayed.

He walked into the restaurant, and Cindy wondered if this was the same Darren she had spoken to the day before. On the dating site, he looked quite handsome. But in person, he looked very different. He was shorter than she expected. His shoulders were stooped.

He sat down and immediately launched into a long, excruciatingly detailed story about why he was late. “My ex-wife’s father died. She’s a jerk,¬†and I never really got along with her parents, but I wanted to stop by to pay my respects. Anyway, my ex wouldn’t stop talking, and I wasn’t able to leave. She wanted to talk to me about a plot of land that we had both invested in. The interest rate had gone up. Blah blah blah blah.”

Cindy found herself nodding, but what she really wanted to say was, ‚ÄúStop talking about your ex! I don’t care about your shared real estate. I don’t care about your ex. Let‚Äôs talk about something else. Anything else. Please!‚ÄĚ

She did interject a few times and was able to briefly change the topic. However, his responses were so disconnected, she began to feel it was a waste of time to talk at all.

The date ended after an hour-and-a-half of bobble-heading, nodding, and counting the minutes, tick tock, until the date was over.

Let’s analyze this!

1. Profiles and photos can be deceptive.¬†Darren’s profile essay and photos were outstanding. But in person, he didn’t match her expectations at all. It’s essential¬†to remember that a profile is not a person. Don’t set high¬†expectations before a date. Even if you’ve had a good first phone conversation, go in with an open mind. The more open you are, the less burned out you’ll become by the dating process. And if a date doesn’t work out, you can say the most important four-letter word in dating – NEXT!

2. Meeting in person ‚Äď the sooner the better. Cindy was smart to meet Darren a day after they first connected by phone. Many people take too long to meet. They talk or email¬†for days, sometimes weeks, before meeting for the first time. This can lead to a faux-relationship, not based in the reality of what it‚Äôs like to actually be with that person. Save time and possible disappointment by meeting right away. Nothing takes the place of an in-person connection.

3. There is no virtue in listening to someone talk about their ex. Cindy should have kindly interrupted¬†Darren when he first started¬†talking about his ex. That conversation not only annoyed and bored Cindy, it kept them in his past and prevented¬†them from learning about each other. Cindy did try to¬†redirect the conversation several times. But Darren didn’t take the bait and continued to talk about his ex. If you’re on a date with someone who won’t stop talking, feel free to interrupt and say something like, “Is there anything you’d like to know about me?” Or change the topic and say, “If we get to know each other better, I’d like to know more about _________. But for now, I’d like to just talk about the two of us.” A good guy will actually thank you for interrupting him.

4. Nervous or narcissist?¬†If he‚Äôs only talking about himself or he’s going on and on something you’re not interested in, he might be doing it¬†out of nervousness, narcissism, or simply because he misses social cues. It‚Äôs sometimes hard to tell on a first date, but pay attention to your intuition. Sometimes, people are so nervous on a first date, they conceal their true personality. I recently heard a great story about¬†a guy who was boring on a first date, but his follow-up email was very funny. The woman sensed that there was much more to he revealed on that first date, and she accepted a second date. They ended up dating for a year and a half! So, if you think there’s some hidden potential and you’ve had an okay time, give your date a second chance. He might surprise you – in a good way.

Have you ever been on a bobble-head boring date? Ever been pleasantly surprised on a second date? Please share your story.

Do you yearn for a true deep partnership with a passionate, loving, grown-up man? Get your free guide to learn the top 3 mistakes midlife daters make, and how to easily turn them around to find a loving partnership. The guide is yours absolutely FREE by clicking here.

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