Why Your Sibling Is Your Best Wingperson

One of my brothers recently became single again and he has made an awesome discovery: Your siblings are your best wingmen and wingwomen. While our other brothers are doing the classic bro thing of going out to bars and chatting up the ladies with him, I live on the other side of the world and can’t contribute in that way, unfortunately. But recently, I managed to wingwoman for my brother — who lives on the East Coast — all the way from my home in Vietnam.

The story starts with Ann Friedman’s newsletter landing in my inbox in early January. (For those of you who aren’t subscribed yet, go and subscribe right now.) Ms. Friedman’s newsletter is packed with curated links to amazing articles about everything from feminism to pop culture to politics and if you pay her just five bucks a year, you also get her hand drawn charts. And there are GIFs. And, at the very end, classifieds — which is where my international wingwoman skills had the chance to shine.

While most of the classifieds in the newsletter are about selling products or services, as you’d expect, the one that caught my eye was from a woman looking for guys to date her best friend. She described her as “5'3" F, 6'3" attitude,” who “lives for second winds” and I immediately thought she’d be great for my brother. I told him about the ad and suggested he email her because, why not? My brother, though, is a busy man and he handed the task off to me.

“It’d be funnier if you did it,” he said — which I knew really meant “I don’t have time for this, Emma, but I am definitely intrigued.”

“You sure?” I asked. “Because you know I’ll do it.”

And I did. I wrote the kind of fawning email that only a loving sister can write about her brother, extolling my bro’s virtues and letting this young lady know that I’d put her in touch, if she was interested. She was; they went out on their first date soon thereafter; and they’re still seeing each other three months later. Boom! Sister wingwoman for the win!

While this story is probably on the extreme end of stories about people hooking their siblings with dates, anyone with brothers and sisters of dating age probably knows that their siblings rock as wingmen and wingwoman. Here are 10 reasons why.

1. They Know You Better Than Anyone

Who knows you better than someone who has known you for your entire life? No one! I immediately recognized a person that my brother would like in the classified ad because I know him and what he likes.

2. They Love You — A Lot

And I wrote such a bomb email (which got him that essential first date) because I love him so hard. My love for my brothers is unmatched: Anyone who has ever had a couple of drinks with me knows that I’m in the habit of showing single girl friends their pictures and making them tell me how handsome they think they are. Only a sibling can fawn over you in a way that’s both complimentary and trustworthy. Seriously, not even your mom can do that, because everyone’s mom thinks they’re the greatest.

3. They’re More Trustworthy Than Friends

Personally, if I was single, I’d be more likely to trust someone who approached me in a bar and was like, “My brother is sitting over there and he’s great and thinks you’re really cute” than someone doing the same for a friend. I don’t know why that is, but it’s definitely true.

4. They’ll Be Critical About Your Prospects

While your friends might think it’s not their business, your brother or sister isn’t about to let you go home with someone totally unsuitable. Our sibling’s business is always our business and we’re not going to sit back and not say anything if it looks they’re about to make a bad choice, whether it's for a one-night stand or a marriage proposal.

5. They’re Your Go-To Source For Info About People Of Their Gender

If your sibling is of the gender you’re attracted to, then they may be a great source of info about that gender. So, for example, my brother has told me that all of my lectures about feminism have definitely penetrated his thick skull and not only helped him when he’s chatting with cool ladies but also have made him a better man. I also can say that I know way more about boys and men than my friends who grew up without brothers do and that knowledge has been invaluable in my dating life.

6. They’re Not Afraid To Embarrass You

Being approached by strangers, whether it’s in a bar or a networking event or online, is always a little bit scary. But you know what’s really helpful for fighting against that fear? Someone else’s embarrassment. Your brother or sister has no qualms about saying embarrassing things about you that will make your potential date feel more comfortable and, believe it or not, that’s a good thing.

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