What was the riskiest thing you ever did?

I told my then girlfriend/Now Wife's boyfriend that they needed to talk, and that she wanted to end their long distance relationship. Face to face. In a restaurant. Not knowing if he was violent, or would try to fight me. He was a pretty athletic guy and he had a pretty good history with martial arts (judo, Ju-Jitsu).


I was involved with a woman for about 4 months, She had lived in another city and moved back home to help out with her aging parents. About 3 years after moving "home", we met and started dating.

On one date, she said "There's only one problem. When I lived in XXXX, I lived with and dated a guy, for 7 years. We were engaged, and then I ended the engagement when I moved home. We've continuted to see each other, but really only see each other once every 2 months or so.

The problem is it's not going to go anywhere. He doesn't want to move here, and my family needs me at home to help take care of my aging dad. It's.. not what the relationship I want, but I cant hurt him".


So, I mentioned that she needed to tell him, and end it as soon as possible so as not to seem like she's cheating on him, and to be fair to me, and our relationship.

Month 1- Nothing,

Month 2 "Did you tell him?" "No, but I will".

Month 3 Same thing.

Month 4- "Look, I dont want to push the issue, but you need to tell him and start the process of moving on. I don't want to be played, and you know you both need closure".

I'll give you a month and then I'll have to move on.

She was really torn. Not being one who dated a lot of men, this guy was really her first serious relationship, and her only "body count". I knew it was tough, but she assured me that she had not had feelings for him in a few years, and they both knew it was destined for failure.

So.. I figured that she needed a bit of help and perhaps someone in her corner as she told him.

I knew where they'd go to dinner, and so I met them there. Unannounced.

I was seated at a table across the room and had arrived prior to them arriving. During the course of the evening, I walked to the table (She looked shocked and afraid something was going to go terribly wrong), and I introduced myself to him.

"Do you mind if I have a seat and join you?"

"Look, I'll be brief. You seem like a really nice guy, and she's explained to me that she's wanting to let you down gently, and to be frank, I'm hoping she's not playing me for a fool, so I wanted to speak with you man-to-man and see if we can get the ball rolling, or to see if I should just walk away".

She and I have been seeing each other for about 4 months, and it looks like we're moving to a more serious stage of our relationship. We've not been intimate yet, and in fairness to you, I've asked her each month if she's told you that she can't continue this, as she's told me she was going to say to you".

I dont want to create a scene, but you two definitely need to talk. She wants to end things with you since you've expressed no interest in moving here, and she wants to move on".

Him: "Is this true?"

Her: "I dont want to hurt you".

Him: Wow.. I had no clue".

Me: "I'm going to go now. I'm sorry, and thank you for taking the moment to listen".

The next day they officially ended.

I gave her space for about a month to gather herself and finish the myriad of phone calls to/from him that were bound to happen.

A year later we were married. (and still are). It'll be 15 years soon.

/r/AskMen Thread