More Funny First Date Stories

Posted by in dating after divorce, first date success, single women over 40 | 0 comments

Do you approach dating with the single focus: ‘I hope he’s the one’? If so, you’re probably frustrated most of the time. Obviously, most dates don’t end in having met the ‘one’. You might be meeting men who are fun, interesting, smart, successful, nice looking, but some key things are missing. Those dates are pleasant, maybe even good, but not great.

BUT THEN…there are those dates that are not at all what you imagined them to be. I’m talking about the dates that leave you scratching your head, wondering if that date of yours is not operating on all cylinders. You know what I’m talking about? 

Last night, at a Holiday party, I was sitting in a small circle of men and women when the topic of my career came up. ‘Dating coach’ is not your typical career, and it’s usually a great conversation starter. Soon the single ladies were sharing their funny dating horror stories.

The following story could have been a stand-up comedy routine.

“I drove a half-hour to meet my date halfway. When I was close by, he called to ask where I was. ‘I’m on exit 37, three exits away.’

About fifteen minutes later, I entered the restaurant. He was sitting at the bar, two drinks next to him. I wasn’t sure if I should appreciate the fact that he ordered me a drink as a romantic gesture, or be angry that he made an assumption about my drink of choice. I decided to let that one go. 

As soon as I walked in, he was all up in my face, ‘Why are you so late? You said you were only three exits away. You should have been here five minutes ago!’ Taken aback, I let that one roll off my back, too, but needless to say, this guy did not make a good first impression.

Bob then began what I’ll call ‘The Bob Show’. As he began a monologue about how cool and amazing he was, I nodded like a bobble-head until I began to get a headache. ‘I have to go to the bathroom’, I blurted out, using any excuse to take a break.

‘I do, too!’ said Bob, and followed me to the restrooms. I couldn’t believe how small the bathroom was; a tiny one-stall room with a small sink and barely any room to move. I finished my business and came out to wash my hands, and there was Bob!

I have never before been scared on a date, but I was frightened. Bob was big, and he was blocking me from leaving the bathroom! ‘What the hell are you doing in the ladies room?’ I asked. ‘Don’t worry,’ he answered. ‘I didn’t hear anything! I just wanted to kiss you’.

‘No, this space is too small. I need to wash my hands. Please move.’ 

When we got to the hall outside the restroom, I said, ‘This date is over’ and went for my coat. 

‘Why’? asked Bob. ‘I thought we were having a great time.”

Has this ever happened to you? Okay, not exactly this, but did you ever have a very funny first date (or second, third or fourth date)? I want to hear all about it.

Please comment below and share your funny stories. We all need a good laugh.

Hey, if you can laugh about the dates that were absolutely crazy, you’ll be more lighthearted when you do meet the right guy. And who doesn’t like a person with a good sense of humor?





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