Wendy and Barry’s Over 50 Dating Adventure

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Wendy was really excited to meet this man who’d contacted her at an online dating site.  It was her first date since her marriage ended almost a year ago.  He seemed perfect on the phone. Plus her friends actually knew him and said he was a really nice guy, so when he asked her to dinner at his home, she was ok with it.

She really wanted to impress this man but as she stood looking at herself in the mirror, self-doubt began creeping in.  She wondered if he’d like her.  She had a pretty face but she’d added a few extra pounds over the years from dipping far too often into the ice cream she’d used to soothe the loneliness in her marriage before it ended.  And that yummy chocolate was now so visible on her body.  She was not happy.

Next she started going through her closet hunting for dating clothes.  Nothing felt right so she ended up in a pair of jeans and a blouse she hoped would hide the effects of her chocolate consumption.

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The excitement Wendy had felt earlier in the day was turning into terror and anxiety, as she got closer to his home.  Walking towards the door, she nearly turned around and left. Her mind was so busy worrying about whether he’d like her and if she’d make a good enough impression to get a second date with him.

Barry opened the door with a huge smile and warmly hugged her.  The first thing she noticed was his bare feet with toenails that were so long and oh so yellow.  Totally grossed out by this but having been taught good manners by her mom, she smiled back and accepted his offer to view his home.  Yet, she was having a really hard time concentrating on his words. She couldn’t stop thinking about those nasty toenails.

He led her through the house and showed her all the wooden antiques he’d collected over the years.  Well that accounted for the mustiness in the air.  Next, Barry began explaining his other hobby and that was collecting old tombstones in his backyard.

Wendy just smiled and let Barry talk. She was feeling pretty creepy hanging out in this house with the old furniture, yellow nails and decaying tombstones in the yard yet she stayed because she felt she just couldn’t be rude and leave.

So they had dinner and she did her best to impress him, listening to his boring stories, laughing when she thought it was appropriate and asking him lots of questions about his life.

After dinner, he invited her into his living room and as they sat and talked, she was trying to figure out how the heck she was going to get out of there.  After about an hour, she made up some excuse about having to leave and headed to her car with a hug and an “I’ll call you” from Barry.

Relieved to be on her way, she drove home wondering how perfection on the phone had turned into such an awful date.  Yet as the next day came and went with no call from Barry about a second date, she found herself disappointed and began second-guessing herself.  Didn’t he like her?  Did she do something wrong?  Was it because she was showing all that chocolate all over her body?  Did he think she was fat?

I would love to hear your ideas on what Wendy did right and wrong on this date.  Also do you have an exit strategy when a date goes bad?  Have you had to use it?  Would love to hear about that too by adding your comments here.

In the meantime get answers to the Do’s and Don’ts of Wendy’s date in Thursday’s Dear Lisa column where you’ll discover exactly what Wendy should have done before that date began, what her exit strategy could have been, and why Barry’s toenails were so long and yellow.

Until next time…

Much love and joy to you. Lisa

The Dating Coach Who Makes Dating Fun And Easier Over 50!

© 2014 Lisa Copeland. All rights reserved.

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Lisa Copeland, the Dating Coach who empowers strong women over 50 to attract quality men, is the founder of Find A Quality Man LLC. To get your FREE Report, "5 Little Known Secrets To Find A Quality Man," visit www.findaqualityman.com.

4 Comments
  1. I don’t want to say that Wendy did anything wrong–blaming her would be a bad idea. She already feels bad about a date that she didn’t really even like in the first place.

    I do think it’s dangerous to go to a man’s house on a first date. I prefer to pick a neutral site, like a coffee shop, and set a date that has a short time span. That way you have a built-in excuse when things aren’t going well.

  2. I agree, no way on God’s green earth would I go anywhere but a public place on a first date. And I agree also, some people hide how boring, odd, whatever, they are better on the phone than in person. So rule number one is enough, meet at Starbuck’s.

  3. I agree with their comments but here is the rub: She walked into this with failure all over her. Instead of relaxing and just having a fun time with no expectations, she found ways to sabotage her experience. A date is not a proposal of marriage. Men realize when someone is scared or judging of them.

    • Yes you are right she did walk into Barry’s home quite insecure because like many women coming out of long marriages, Wendy wasn’t sure how to handle dating. Her lack of confidence really got the best of her and she gave her power away to this man she didn’t even like which is very common. We as women hate rejection even when we don’t like the man which is what happened to Wendy after that date. So appreciate your comment. Thank you!

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