When Your Best Friend Dates Your Brother

Aww look at this picture, Rachel, Garrett is the epitome of heart-eyes emoji and you’re just….oblivious. Photo credit goes to Yury Kim, thanks bro for taking so many photos over the years even when we hated it.


Rachel has always assumed that was my reaction when Garrett told me that Rachel and him were dating. Though admittedly that word was said, it was meant to convey more confusion than horror. You see, I knew that my brother Garrett liked Rachel. However, I was under the impression that she did not.

“No, really? Like really? But Rachel likes pro-active guys? Well you’re not exactly pro-active um uh Garrett.”

That was my reaction to my flabbergasted brother (I’m sorry that I didn’t believe you Garrett. I love you. Hopefully you’re not bitter still).

It is somewhat a weird experience when your friend decides to go and date your brother. However, you can make it weirder depending on how you react to it. So, to help you make it less weird, here are three things that I have learned through this process of my best friend dating my brother.

Their new relationship is not a big deal but be prepared to have those important conversations. As soon as Garrett left after telling me that Rachel and him were dating, I immediately went to Facebook messenger as you were in Chicago (I may have gone overboard with All-Caps) to talk to her. We started a long, good, and intimate conservation over social media, about Garrett yes but we also talked about Jesus, being humble, and whether people had a shadow of goodness because they are created in the image of God (we like to go deep). We have only had a few conversations about their relationship. That was intentionally established in the beginning which leads me to my second piece of advice.

Continue to see them in their separate identities (best friend and brother) as well as their new identity (couple). Rachel and I were friends before Garrett came on the scene. When Garrett came onto the scene, Rachel wanted to continue to see me as a friend instead of possibly future-sister-in-law material. Which was why she didn’t really talk about Garrett. So even though the three of us hung out, Rachel and I actively pursued meeting as friends and not as oh-future-sister-in-law-material (though you are my favourite potential sister-in-law Rachel). Don’t get so caught up in the new relationship status change because….

At the end of the day, it is their life and their choices, and it has very little to do with you.  Because I’m close to both of Rachel and Garrett, I know a lot of their ups and downs. However, something that I’ve learned and am learning is that their relationship has nothing to do with me. It was my brother’s choice to keep on pursuing Rachel, even when she was completely oblivious. It was Rachel’s choice to go out with him. It was their choice to continue their relationship overseas and through Skype calls. Yes, I get to witness it. However, this is not about me. This is not about you. Let them figure out what they need to figure out.

Actually, it’s not so weird after all.




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