I’m a male in my late 40s that is relatively successful and I have an interesting life filled with lots of travel, art, and activities. I stay fairly healthy and don’t seem to have any issues attracting women.
However, i struggle with dating.
This week I was in London and a friend of mine set me up with a friend of his.
We all had dinner and she was coming to me hard. She was beautiful and we ended up kissing a lot and making out. She asked me to get together the next night. She also stated she wanted to travel with me the next time I’m in London.
Well, the date is going well and we’re chatting about travel. I decide to extend my stay (i’m working abroad) and ask her to go to another city with me. Totally random! She agrees and we book the plane and hotel.
Well, the flight cancels over night. I need to book something quickly as the trip is the following day and flights are disappearing rapidly.
I go ahead and book a flight and give her the details. She balks a bit and then proposes another flight from a different airport.
After a bit of back and forth I said this isn’t going to be fun planning such last minute. Let’s just take a train and go somewhere easy. In truth, i knew I was putting too much pressure on this right away and I knew I was blowing it.
Anyway, She agrees that its complicated, but then cancels the whole plan, even my offer to take a train to the coast
I know I dropped the ball on this, and put my friend in an awkward situation. I also broke my rule against mixing work and dating.
What’s done is done, but I’m looking for feedback on how I can prevent this type of over reaction in the future.
4 comments
Oh you already said it was over reaction.
Maybe just don’t date over reactive females? 🤔
I had a similar situation with my boyfriend, we planned that I travelled to him late Feb but dude never could confirm a plan with me – typical ENFP.
I finally ran out of my patience and told him if he didn’t want me to come, he should just say so.
He then explained his reason why he couldn’t confirm because his work schedule was all over the place due to his business partner just had his first baby.
I was surprised .. he could simply have told me so I would understand him instead of getting upset.
Then he said he wanted me to come so badly..He valued me so much and my honesty .. he hoped I would just wait, he’d arrange everything including air tickets when things at work were settled.
I said: sure babe, looking forward to seeing you!
Valentines Day dude texted 11:58pm my time telling me : hey babe just jumped on the plane back to Melbourne had a great success in Sydney with work. I wish I were there to spoil you today xx
I am happy with a text like that. Means more than a bunch of flowers or a diamond ring to be honest.
Personality wise, I don’t suggest travel plans unless being asked. I just go with the flow, whatever the guy plans is gonna be the perfect plan.
Honestly, it’s freaking rare men actually plan. Many go through life aimlessly.
You came on too strong, too fast. Didn’t give her space to chase you, to wonder how much you really like her. Not enough uncertainty.
Next time take things slow. Get to know her but conceal your interest level. Girls say they do but actually don’t like being your #1 priority in life, it’s off-putting for them, so put your hobbies, goals, etc first and don’t see her too often.
She sounds like a user. You were supposed to be responsible for doing everything and the moment she had to put any skin in the game she started, for all intents and purposes, pouting.
Your mistake was in not dumping her the second she showed herself to be a spoiled princess type.
You got fucked by a flight cancellation, nothing more.
Spontaneity, risk taking like this is fine when inspiration hits the two of you. But when you’re gambling, luck has to go your way.
Naturally, the two of your hadn’t had time build something strong enough for rough seas, too don’t beat yourself off over it sinking.