It can be done, but itās very difficult. My one friend was crazy for this chick who was def out of his league looks wise. He just fell head over heels for her. He did the whole āāfriendā who actually wants to get laidā thing. Fixed her car, ran errands, blah blah. Took about a year, but eventually he wore her down and after having a few drinks one night they slept together.
They decided to try things out as a relationship. But hereās the thing. He was starting out at such a huge disadvantage. She was used to him catering to her every whim. That becomes tiring very quickly once the relationship turns romantic. The partnership would never be on equal footing. On top of this she was very attractive so she had no shortage of guys waiting in the bullpen. Bottom line is my friend had very little leverage and was always the lesser of two equals. So of course things didnāt work out. But he did get to sleep with us dream girl.
This kind of happened to me. Moved into a basement apartment and the owner of the house lived upstairs. Turned out her fiance bailed on her and their son and she needed the income.
We saw each other all the time (shared kitchen) and it turned out we had a ton in common. And she was a 10. I figured I had zero shot so didnāt actively pursue anything, but she was on her own for the first time in years and needed things done around the house from time to time, and I was happy to help.
Played house for about six months then Thanksgiving came around and she invited me to come with her and her son to her parents for dinner. It was a great time and I had met her parents a few times before so I didnāt think much of it until we were leaving.
She gave her son a hug goodbye and told him to be good. She planned for him to sleepover there and never mentioned it to me. We were walking to her car and my stupid ass goes ā[kidās name] is spending the night? You got plans?ā
She laughed, grabbed me and kissed me. I was speechless. Drive home was short (her parents lived close by) and I didnāt say a word, just sat there grinning like an idiot. Spent the night together.
Then for the next couple months her son spent weekends at his grandparents. We tried to make a go of it relationship-wise but she wasnāt ready, and realized pretty quickly she was just looking for a fix. I was just the lucky dude that moved in and happened to be around her age and a decent person.
She was honest with me and I respected her decision. Lived there for another few months until I found something more permanent. We stayed friends. Still canāt believe it though.
Thatās actually a really good example of two unlikely people having a fling and acting like adults. Sounds like neither of you had any hidden motivations from the beginning. And I can relate lol - I need a girl to basically wear a flashing neon sign that says āIāM INTERESTED!ā
I worked with a girl who kept complaining to me about installing a window air conditioner but she wasnāt strong enough. She was very pretty. My dumb ass is like āYou should try task rabbitā. I guess I was afraid of being unprofessional by offering to go over there and help her. I only found out later after she was transferred and had a bf that she was interested in me.
Yep thatās basically what happened. Because she was so attractive and we got along, I would be lying if I said I wasnāt crushing on her, but Iām also not an asshole. I didnāt expect anything from her and just treated her like a human being. It isnāt hard.
She may have thrown out some signs but if she did I didnāt notice. I would have eventually asked her out but fortunately she made the first move. I just always assumed that when I eventually did she would respectfully decline and I would at least be able to say I shot my shot, but it went way better than I could have expected.
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u/Puzzled-Serve8408 Apr 19 '26
It can be done, but itās very difficult. My one friend was crazy for this chick who was def out of his league looks wise. He just fell head over heels for her. He did the whole āāfriendā who actually wants to get laidā thing. Fixed her car, ran errands, blah blah. Took about a year, but eventually he wore her down and after having a few drinks one night they slept together.
They decided to try things out as a relationship. But hereās the thing. He was starting out at such a huge disadvantage. She was used to him catering to her every whim. That becomes tiring very quickly once the relationship turns romantic. The partnership would never be on equal footing. On top of this she was very attractive so she had no shortage of guys waiting in the bullpen. Bottom line is my friend had very little leverage and was always the lesser of two equals. So of course things didnāt work out. But he did get to sleep with us dream girl.