Not that you need permission, but definitely consider their feelings and their point of view. If you break up down the line, keep the details of the breakup to yourself. One thing led to another and six months later here we are. It was definitely weird at first and my family would often crack jokes about it. Who wants to picture their sibling getting busy with anyone, let alone with your best friend? He lied to me for years about their relationship while I knew they were into each other. So, yeah, that worked out. Friend turns out to be a big asshole, me and the sister start dating. However, she adored my family, so she continued to hang around with them - parents, brothers, etc. We date a couple years, I start attending family events regularly.
Handle it in a mature, discreet way so that all parties can remain friendly afterwards. A girlfriend of mine found herself in this predicament. I was shocked to learn that she had feelings for me since second year college. Her sister has been the most helpful person planning our wedding. I can see how it would get tricky and, possibly, messy. We had a mutual break up after a few months and remained close afterwards. Friend turns out to be a big asshole, me and the sister start dating. He lied to me for years about their relationship while I knew they were into each other. My sister has been dating an ex of mine for the last two years, and the ex has plans to propose to her at the end of the year. It was definitely weird at first and my family would often crack jokes about it. But imagining my girlfriend talking to me about kissing, getting intimate or even hating my brother would probably leave me feeling a little uneasy. Her sister starts becoming more comfortable around me, sees me as a brother now. Meet her friends, turns out her and her sister hang in the same group. Everyone is lighthearted about it and my wife makes jokes all the time. We date a couple years, I start attending family events regularly. We have been together for eight years now, married for 2. She set me up with her younger sister and things were going great until she cheated on me. One thing my girls and I did growing up was talk about the boys we liked, dated, kissed, hated, and then kicked to the curb. Make sure the guy in question actually likes you as much as you like him. However, she adored my family, so she continued to hang around with them - parents, brothers, etc. We broke up, and my SO was on my side of the whole thing and completely supportive. I never told him I knew until a while later when he asked me if they could be together, and lied to my face when I asked if they had ever been physical. When we were broken up she cheated on me at college but still talking we got into a fight, and during the fight she told me she had sex with my brother. If you decide to date the guy anyway, keep your friend out of your relationship. My current SO significant other and I were very close friends in high school and we would always set each other up with dates and stuff. What if they break up?
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