A Date From Hell What Should You Do When He Does THIS

October 11, 2010 by  
Filed under Dating Tips For Women

I want to share this date-from-hell story of a subscriber of mine, and I think that probably half of you will say you’d have done the same; and the other half will say they wouldn’t have known how to handle the situation. So, if you don’t know how to handle a situation similar to this, read on.

I trust it will be enlightening read and will help you in your relationships with any man you date and have a relationship with along the way. If you have a story you want to share with me and my readers, send it to support [at] why-he-doesn’t-call.com and I may post your story on this blog or my other blog.

Here is the email from my reader:

Hi Elaine,Bad Date

I have been reading your e-mails for a couple of months now, and I also bought your book Should I Text Him and Confidence Tips. I consider myself to be a shy person, and I am recently divorced and just getting back into dating so your book on confidence helped a lot. I want to share my story and hopefully get your opinion on this guy I just met on a dating site.

This guy Dean contacted me on a dating site. He is 30 y.o. and I am 41, but I look young for my age and he didn’t seem to have a problem with it. I wouldn’t normally date younger men but this guy is handsome, in great shape, has a great career and education, and he seemed like a mature man so I agreed to go out with him one night.

We met at a local restaurant. It was on a Tuesday night, so neither one of us was dressed up, we were both dressed rather casually.

 He seemed a little bit shy, but pleasant. We had dinner and went to another place for drinks. I had more to drink than I should have so he gave me a ride home because I didn’t want to drive after three drinks. He made sure I made home safe by walking me to the door of my condo and left.

The following day he texted me saying that we should meet again, to which I agreed. We set up a date on a Friday and he said he’d come pick me up so I could have a drink.

He picked me up and offered to go to a restaurant in the city. I know I should have said let’s go some place local, but I thought it was a good idea and I haven’t been to the city for a while so I was excited about it.

That’s when the problems started.

Almost immediately I noticed that he started acting differently. For one he was over-dressed, wearing fancy outfit and expensive shoes. He also walked differently, the kind of ‘macho’ walk, not really normal but very pompous, and driving on the freeway he drove like a lunatic weaving in between cars, accelerating needlessly and going well over the speed limit.

I told him his driving made me nervous and he reassured me he was a good driver instead of slowing down, which frankly didn’t make me feel any better.

When he got to the city he parked in the parking garage of his office building and had to walk a few blocks to the restaurant. On the way he made sure to walk by the building in which he owns a condo which he is now renting out and to show it off.

It was kind of funny to see how this young guy was huffing and puffing trying to show off. I am no longer in my twenties so I was not impressed but I allowed him to do whatever made him feel better.

But when we got to the restaurant he really showed his true colors. He was rude to the bartender because it took her a few minutes to get to our order. He seemed very impatient and was mean to her, muttering that she was too slow to make us drinks.Date From Hell

He immediately had a double shot of Tequila, and a glass of beer to wash it down. He also insisted that I have a shot, and only after my repeat refusals he got off my back.

Finally we got seated at a table. I told him I wasn’t really hungry but would have some appetizers.

When the food arrived he insisted that I eat more, and said that it was weird that I wasn’t eating as much. I asked “does it bother you?”

He said “yes, it’s weird” with a very mean facing expression.

I said, “if this bothers you, perhaps we shouldn’t go out”. “Maybe so,” he said. Then he left to go to the bathroom and came back ten minutes later.

When he came back he apologized, and I said, let’s just move on.

I already regretted agreeing to meet up with him, and I know I should have left but I didn’t.

It got worse from there.

He texted his friend who lived in the city and wanted to meet up. That was fine by me, especially because I was hoping that hanging out in the city and having a walk would have made him sober up before we drove back, so after we had dinner we picked up his friend in downtown.

His friend seemed like he belonged in a gang. He brought a girl with him, whom he referred to as “a friend with benefits and she doesn’t mind”. Nice!

So, we are driving around not knowing where to go. Next thing I know, I smell weed. I turn around, and this guy’s friend is smoking a joint. Next, my date picks up a joint, and they pass it around. We finally park on the street by his place which he is now renting hitting the curb and a trash can in the process.

Guy SmokingWe go up to the roof top of his building which has tables, chaires, and even restrooms. So, we sit there, and his friend pulls up three more joints and a six pack of beer.

At this point I just want to go home, but it’s past midnight now and I don’t know how I am getting home because the train doesn’t run this late.

After smoking three more joints and finishing up the six-pack my date is inviting everyone back to his place in the suburbs where we both live. We go downstairs and he brings the car. I am hesitant to get in the car, in fact I know I am not getting in that car! Everyone else gets in and I am standing outside. Then my date yells at me “Get in the car!”

“I don’t think so,” I say and walk away. So, I am walking down the street and they are driving next to me telling me to get in.

I ran into the nearest bar and hide till they leave. Of course, I had to take a cab. I don’t know if the guy ever made it home.

What do you think of this, Elaine? A date from hell! What was my mistake, and what should I have done?

I hope to hear back from you!


Hi Kat,

First, I want to say you did the right thing by not getting in the car. Secondly, I understand it’s only your second date, and you never know who the guy is until he shows his true colors. With that said I think you should have left when it was already clear that the guy was rude and mean to other people, and you as well.

He is also very immature regardless of his education and a good job. He also shows temper, controlling tendencies and anger management issues.

I would have left a lot sooner, but I understand if you didn’t want to stir the pot.

In any case, live and learn. Perhaps next time you should stay closer to home until you get to know the person better.


Do you have a date-from-hell story you want to share with me and my readers? You can share it here in the comment section or send it to me!

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4 Responses to “A Date From Hell What Should You Do When He Does THIS”
  1. Robert says:

    Well Kat and Elaine, our positions in life are much different, in that as a man, I can go almost anywhere with anyone and be safe generally. Since nothing happened (due to your good judgment) it’s little more than a funny story. You did the right thing. That situation could easily ended up with a date rape, or a drunken wreck where someone was hurt or killed. People are weird and you ladies need to take precautions in case the date doesn’t work out or the guy is a psycho..

  2. morry says:

    hallo your name?

    please you like write computer me facebook ok good
    i like speak senang you ok
    where you from?

    thank you

  3. Rangela says:

    Date means understanding two new friends that her understod both and i think being his new life . but i respect my parents his say anything i aproved. because his my God.


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