Would You Still Date Him If...? The Dating Red Flags That Started a WAG Debate

Some questions have an obvious answer.

Would you date someone who treats you badly in front of his friends?

Absolutely not.

Would you date someone who likes every girl’s Instagram post?

Okay… now we need context.

Would you date someone with a girl best friend?

And there goes the entire podcast.

On this episode of the WAG Podcast, Angelina, Annabella, and Scarlett played “Would You Still Date Him If…?” — putting dating red flags, relationship dealbreakers, social media habits, jealousy, friendships, and a few extremely specific scenarios up for debate.

The rules were simple.

Someone gives a scenario.

Everyone decides: Would you still date him?

The opinions? Not nearly as simple.

Would You Date Him If He Likes Every Girl’s Instagram Posts?

The first question immediately exposed the problem with dating red flags: context matters.

If he’s liking his sister’s posts? Obviously fine.

A longtime mutual friend? Probably not a big deal.

But if he just met one of your friends and suddenly he’s liking every recent post she uploads? That’s when things start feeling a little more suspicious.

The conversation quickly became less about whether someone pressed a heart on Instagram and more about why they’re doing it. Because sometimes a like is just a like. And sometimes… you know exactly what that like means.

Would You Date Him If He Checks Your Location Every 10 Minutes?

This one should have been easy. Checking someone’s location every ten minutes? Weird. Everyone agreed.

For approximately ten seconds.

Then came the confession: “Yeah, I track my boyfriend all the time.”

And suddenly we had a problem.

There’s a difference, the girls decided, between checking someone’s location because they’re traveling and you want to know they arrived safely — and watching the little dot move across the map like you’re working air traffic control. One of us apparently checks turns. And speed. And where the car is going. We’re not naming names. The podcast already did that.

The Mama’s Boy Question Got an Immediate Answer

Would you still date him if he calls his mom about everything? No. This one barely survived long enough to become a debate.

The distinction was important, though. A guy who loves and respects his mom? Huge green flag. Someone who’s kind to his parents? Even better. But there’s a difference between loving your family and relying on your mom for every decision in your adult life.

As Angelina put it: “I’m not dating the mom.” Enough said.

Then We Got to the Girl Best Friend

This was the question that changed the episode.

Would you date a guy who has a girl best friend?

Suddenly, nobody was giving one-word answers anymore.

There’s an obvious difference between having friends who are girls and having one girl who is the first person he calls, constantly texts, hangs out with, and treats as his closest relationship outside of his girlfriend. That’s where the opinions got stronger.

One argument was that a respectful friendship shouldn’t automatically be a problem. Another was that if the girl best friend genuinely wants to be friends with the girlfriend too, the dynamic feels completely different.

And then Angelina dropped the line that basically ended any chance of a calm discussion: “The only reason I would be girl best friends with a guy is if I had a thing for him.”

Chaos. Ryan was immediately excluded from this statement because he’s “like a brother.” The hypothetical girl best friend? Not so lucky.

Apparently Jealousy Is a Green Flag Now

The girl-best-friend debate quickly turned into a much bigger conversation about jealousy. Is jealousy always toxic? Or is a little jealousy normal when you actually care about someone?

The distinction wasn’t about controlling who your boyfriend or girlfriend can talk to. It was about whether you care when someone is obviously flirting with the person you’re dating. And according to Angelina — if another girl is flirting with her boyfriend directly in front of her, we’re apparently entering an entirely different genre of podcast. We’ll leave it there.

Would You Date Him If He Still Lives With His Parents at 25?

This one started as an immediate no… and then became more complicated. Because living at home isn’t necessarily the issue. Someone could be saving money, finishing school, helping family, building a business, or working toward moving out.

The bigger question was: what’s the plan?

There’s a difference between living with your parents while actively building your future and sleeping until 3 p.m., playing video games all night, and having no intention of changing anything. The address isn’t necessarily the red flag. The lack of ambition might be.

Treating You Differently Around His Friends?

Next. Seriously. This was one of the fastest answers of the episode.

If someone becomes less affectionate around friends, that’s one thing — people act differently in different social situations. But if your boyfriend becomes rude, dismissive, or makes you feel small because his friends are around? No debate necessary.

Then Someone Admitted to Having a Fake Account

Would you date someone with a fake Instagram account for checking up on people? We probably shouldn’t judge this one. Because apparently… we have them too.

What started as another hypothetical immediately became a series of confessions about spam accounts, hidden Instagram Stories, and one very memorable investigation that revealed someone who claimed to be single… was not.

Maybe don’t take social-media advice from us.

The Most Important Dating Skill: Changing a Tire?

Somewhere along the way, “Would You Still Date Him If…?” became: does he know how to change a tire?

According to Angelina, this is apparently non-negotiable. The logic? If you’re stranded on the side of the road and call your boyfriend for help, hearing “I don’t know either” isn’t exactly the rescue scenario you were hoping for.

That led to an even better story about a dad receiving a text that his daughter’s boyfriend couldn’t change her flat tire. Step one? Dump him. Step two? Dad’s on his way.

And Then We Learned Bella Googled How to Hug a Guy

We don’t know how we got here either.

Bella admitted that she once watched a YouTube tutorial about how to hug a guy. With Dad present.

One tutorial suggested a normal side hug. Dad approved. Another suggested jumping into the guy’s arms and wrapping your legs around him. Dad had a whistle. That suggestion did not pass inspection.

And somehow that wasn’t even the full confession — Bella also looked up how to hold hands because she wanted to know which way your fingers were supposed to go. Apparently dating has tutorials. Who knew?

So What Actually Makes Something a Dating Red Flag?

After twenty minutes of arguing over girl best friends, Instagram likes, location tracking, parents, independence, jealousy, fake accounts, flat tires, and proper hand-holding technique, we came to one conclusion:

Dating red flags aren’t always as simple as the internet makes them sound. Context matters. Intent matters. Respect matters. And sometimes the exact same behavior can feel completely different depending on the relationship.

Would we all date the same person? Absolutely not. Which is probably a good thing.

But there are a few things we agree on: treat people with respect, don’t become a completely different person around your friends, have goals for your life, and maybe… learn how to change a tire. Just in case.