Men tell the boldest thing they have ever done to tell a woman they're interested

All Woman

MANY of us have pushed the limit or gone against the status quo in our lives. And sometimes choosing to go against the tide may work in our favour, and other times it doesn't. For a few of our male readers, when asked about the boldest thing they've ever done to express their interest in a woman, many of their choices worked in their favour, but others left them cringing.

Below they share their bold moves with All Woman.

Tariq H, 31:

I stole a kiss straight on the lips.

Garth Y, 43:

I'm usually just upfront about how I feel, but this ex of mine was in a relationship and I just barefacedly told her to leave her man. This was after I pursued her for a little while. She wanted the relationship with me, so telling her that influenced her decision.

Sean S, 37:

I remember just before leaving high school I used to be friends with this attractive classmate. We would chill and have long conversations after school. I was really attracted to her and I really liked her. So one day I decided I would write her a letter to let her know how I felt about her and that I wanted more than a friendship. I slipped the letter in her bag, hoping that she would see it and be like, “I have the same feelings too.” Bwoy, was I wrong! She told me that I was too young for her (we were the same age) and I couldn't 'mind' her (truth). It did hurt me, star, but now I am happily married to a drop-dead gorgeous woman.

Francis D, 39:

Before the day of #metoo I went up to a girl I liked, hugged her and kissed her. She was surprised at first, but then she kissed me back and the relationship blossomed.

James E, 33:

The boldest thing I ever did was approach a woman's friend in a club and start a conversation with her, so I could meet her friend.

Lennox T, 46:

My boldest move was asking my now wife for her hand in marriage. It was bold for me because that is a big step.

Merrick W, 26:

I told her mother right in front of her that I wanted to be in a relationship. The reaction was pure laughter.

Miguel F, 39:

“I'd like a threesome with you.” She said, “Sure, for your birthday.”

Christian R, 27:

I invited her out and told her that I wanted to be with her and it worked. Please note her blushing and acting shy were part of the act.

Germaine L, 41:

There was a girl from one of my church's branches whom I liked but didn't know how to tell her. It so happened that she came to camp and we ended up in the same sports house so we hung out more. When I got back from camp I wrote her a letter and sent it off. But I ended the letter by saying, “Jah know mi rate yuh gyal.” After I mailed it and a couple weeks passed and she didn't respond (I had put my house number in it) I thought about it and realised that what I wrote at the end was stupid. In those days there was no social media, but she eventually called and I apologised for what I said at the end of the letter.

Anthony E, 29:

While I was an undergrad student at UWI, I dated a girl who was also a student at UWI but before we got serious I would allow her to sleep over in my room when we studied late, buy her groceries, and allowed her to use my stuff. Eventually we got together and it lasted for over a year, but the end result is that she ended up dating my friend.

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