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I Had A Crush On My Best Friendís Brother & This Is What Happened

Storytime: How I Started Dating My Best Friends Brother!???!

Although this date has gone down in history as just that, celebrated annually as our friendship-a-versary, there was something else about this day that changed my life forever: it was the first night I met her brother. Standing awkwardly outside of a local laundromat, I watched as this guy pulled into the parking lot to meet us. He was extremely tall, towering over me at six feet, two inches, and had that teenage bad-boy look to him. I was intimidated. I expected him to be as obnoxious and annoying as the friend he brought with him, who was making mean jokes and play-fighting with Leslie. He stood a distance away from us, his eyes shyly focused on his feet. Leslie dragged me inside, wanting to get away from the boys, and we sat on a bench and talked until her brother stood in front of me and put out his hand.

Umm, who's this about? Did he get back together with his ex again? Ugh, I'm going to have to go to this wedding, aren't I? The more I thought about it, the more I realized how badly I wanted it to be about me. Don't get me wrong.

I didn't want to be the girl who hurt him but I wanted to be the one he cared enough about for that to be possible. Maybe the one who went on a date with someone else recently?

Reader's Dilemma: Will Dating My Best Friend's Brother Ruin Our Relationship?

I had to know. I slid into his DMs although, I definitely didn't call it that in and boldly asked if his status was about me. I knew it was. It had to be, right? We'd shared glances when I took over his living room on a weekly basis to host study groups with Kristie. And there was that one time he pretended to be my date so no one would hit on me because I was already having a crappy day.

My best friend's just started dating my brother. A recipe for disaster, no?

It's just that, I figured it would be years before either of us admitted we had feelings for each other. There was the age difference and the family complications and the distance and just, literally everything else that made it seem not only impossible but also ill-advised. On his boat. Full disclosure: I most definitely was not. But Michael didn't need to know that.

Dating my best friends brother

My little white lie worked. He admitted that the status update was about me.

I swooned. We stayed up talking for hours that night and almost every night after that for the four years we were together. I'm not going to lie.

It was awkward at first ó not between us but for the people around us. I'd been friends with Michael's sister for about seven years by this time and our families knew each other exceedingly well. So, you could probably guess that my parents weren't thrilled to find out that the only person they trusted to take Kristie and me to a nightclub for the first time I grew up in the Caribbean, where the legal drinking age is 18 was now my boyfriend. It was this weird dichotomy where they truly trusted him with my life, just as long as we absolutely were not dating.

I'm not sure where I got the gumption to do this, but I decided that Michael and I would proceed as if everyone was as excited about it as we were, until they were, and it worked.

It's been more than five years since we broke up and my parents still openly talk about how he was the best guy I've ever dated. Thanks, Mom and Dad. I'm glad we have similar taste in guys? I don't know.

Obviously, similar taste in guys wasn't something Kristie and I had in common since, you know, I dated her brother. She never openly questioned our relationship, but there were times I felt like it pushed us apart, particularly toward the end of it. Michael and I had one of those year-long breakups that lingers way past the actual expiration date of the relationship.

No one cheated, or fell out of love, or anything dramatic like that. But, being almost 10 years younger than Michael was, I felt like I needed to go off on my own for a while.

I'd gone from living at home with my parents to living in my college dorm where I Skyped my hometown boyfriend every day for four years. In a lot of ways, dating my best friend's brother was what kept me feeling close to home when I felt most alone. You could say that Kristie was kind of like our lifeline. So, when Michael found out that I'd moved on more than a year after our breakup and that she'd neglected to tell him, he took it pretty badly.

I could feel the cosmic shift in my friendship with Kristie almost instantly. In trying to support me as a friend, she'd failed him as a sister and now, she had to do major damage control, which meant not-so-subtly implying that I should remove myself from the equation.

It always comes back to high school math, huh? I was intimidated.

I expected him to be as obnoxious and annoying as the friend he brought with him, who was making mean jokes and play-fighting with Leslie. He stood a distance away from us, his eyes shyly focused on his feet. Leslie dragged me inside, wanting to get away from the boys, and we sat on a bench and talked until her brother stood in front of me and put out his hand.

He was holding a little teddy bear keychain that he had got from one of those candy dispensers that shell out prizes instead. The conclusion I had come up with was nothing compared to the future that was in store for either of us.

Or to be even more specific; her best friend's brother. She thought she had everything worked out, she had her plan, she had the date of when she was leaving. Readers give their best tips on how to date a friend's family member. The story of how I navigated dating my best friend's brother. Follow my path to engagement in such a strange circumstance.

That was the beginning. That was a lifetime ago. When I think about it now, a mixture of sadness and nostalgia drown my being. What I would give to go back and see if I could have avoided such a mess.

To see if it would have made much of a difference if time allowed me a do-over. After our introduction, the more I would spend the night, the more he would joke about us being together. I ignored it, they were only jokes.

One reader is "disgusted" that her best friend has started dating her brother. Dr Petra Boynton, the Telegraph's sex and relationship agony aunt. I would spend my college years dating while Michael worked through his . In a lot of ways, dating my best friend's brother was what kept me. "There's no greater compliment to my character than a friend allowing me to date their sister.". The first whisper reads, "Sibling rule: If you wanna be ".

But jokes turned to more jokes, more jokes turned to feelings, and the rest is history. There was only one problem. Apart from the blood ties that make you love your family, siblings have a tendency to despise one another.

In this case, the rivalry was the equivalent of a third World War. They would fight and of course, your friend expects you to have their back. But so does your boyfriend. Whosever side you took, you would still have to face the wrath of the other person.

August 31st, was the first night I ever spent the night at my best friend Leslie's house. Although this date has gone down in history as just. Is three a crowd if it's you, your boyfriend, and his sister/your best friend? Should our reader take a chance on a relationship with a guy if his. Q: Hi, what are the pros and cons of dating your best friend's brother? Particularly when you have struggled with infidelity in the past, your best.

It was a lose-lose no matter what I did. That was one issue. Then I had to consider splitting time spent between the two. Another thing to consider: you want to tell your best friend everything, right? Well, hearing about your romance with their brother is NOT something that perks up their ears.

Ask Shallon: How To Date Your Friend's Brother or Cousin!

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