Ask Mom & Spawn!

Ask Mom & Spawn: Should I Date My Best Friend?

Friend or Future Husband?

“Hola! My best mate since my first year of college (UK System) told me we should be a thing (a couple). He Dropped this massive bombshell on me, I don’t even know what to say. We’ve been best mates for over 5 years, and now I don’t even know what to do!!! We know pretty much everything about each other and there’s no bullshit in our friendship. He says we would make a good couple, but I just don’t know what to do. We have joked about being each others back up plan; if we are still single by the age of 35 then we would end up getting married. The thing is he has dated two of my mates, and if we do become a couple, I don’t know how to break it to them. My sister agrees with him and pretty much said the same thing as him. Especially the part when he said, if we don’t work out, we would still be best mates. I need a third party involved in this situation…” – Sammy

@CrazyJewishMom: Go for it! Your eggs aren’t getting any younger!

@KateFriedmanSiegel: Your eggs are fine, Sammy. To your question, friendship can be an amazing foundation for a relationship. My best friend is marrying a great guy (i’d call him her soul mate, if I believed in soul mates) who she was friends with for 7 years before they started dating. 

@CrazyJewishMom: You see? There’s no such thing as a platonic relationship after the age of 15! Sammy, you’ve both obviously been wanting to fuck each other’s brains out but just haven’t had the chance yet.

@KateFriedmanSiegel: Okay then, mother! Before you jump into bed though, you do need to recognize that this is a big decision. Right now, it’s easy to say ‘even if we don’t work out, we’ll still be friends’, but a lot can happen over the course of a relationship. People cheat! People lie! People decide to get giant face tattoos and join scientology! Anything can happen, so you should go in knowing that there is some risk of losing the friendship. 

@CrazyJewishMom: Yeah, you could also get hit by a bus tomorrow. Go for it.

@KateFriedmanSiegel: I agree. Even with that risk, I think it’s worth exploring. The downside? You may lose a good friend. The upside? You could fall madly in love and have a deep, meaningful life with someone who is truly your best friend!

@CrazyJewishMom: Uch! Enough with the cheeseball advice, spawn. I’m going to throw up. Sammy, just go for it already! 

@KateFriedmanSiegel: Wait! The question about your friends who also dated this guy is a super tricky but important one to answer. Generally, I think it’s a terrible idea to violate #GirlCode and date a friend’s ex. That said, I can easily think of a few guys from my past who I would be thrilled to have friends of mine date! Things are messy in college, and it can be complicated. 

@CrazyJewishMom: Yeah, but who would want to date your loser, bedwetting exes! 

@KateFriedmanSiegel: Mother, it was ONE guy! 

@CrazyJewishMom: One is enough. 

@KateFriedmanSiegel: Anyway, it’s tough to answer this one without more information, because it really depends on how seriously he dated your friends, how those relationships ended, and how those friends actually feel about him now. You don’t want to date a guy, if your friend is still building love shrines for him in her closet or stabbing a voodoo doll with his name on it. At the same time, you don’t want to refuse to date this guy on principle, if your friend genuinely doesn’t care. 

@CrazyJewishMom: OMG! I’m sure your friends already know ! They’ve probably seen you eye fucking for months.

@KateFriedmanSiegel: You know your friends and the dynamics of your friend group best, so if you think they might be okay with it, it’s worth talking to them. But if you actually think it would hurt them…i’ll quote the wonderful (admittedly fictional, but still amazing) Leslie Knope: “Ovaries before brovaries.”HIRES BOOK COVER

Read Kate’s Book!
Need advice or have questions for @CrazyJewishMom & Spawn? Submit them via the form below, and we just might answer!

Your Name (required)

Your Email (required)


Your Message


By making this submission, I hereby acknowledge that I have read, understand, and agree to all the terms and conditions set forth herein.

Follow us!

@CrazyJewishMom on Instagram, Twitter, and Facebook!
@KateESiegel on SnapchatInstagram, Twitter, and Facebook!

The Latest

To Top