10 Dating Red Flags in Friend Groups

Advice for a reader who wants to scout out good partners without apps.

A Cattywampus reader wrote in for advice with the following question. You, too, can submit questions for me to answer here in my newsletter. Just email me and make sure the word ADVICE is in the subject line. I am heatherannehogan at gmail dot com.

---

Hey Heather,

I have a terrible record of choosing awful people to date! I have dated some nice people and our relationships didn’t work out for various reasons, but I keep making really bad choices in romantic partners! I’ve just moved to a new city and I’m making new friends. I’ve decided I want to learn how to scout out what might make someone a good romantic partner before dating them. Please don’t suggest the apps. I am v. v. bad at the apps. Please don’t tell me to “listen to my gut” or “follow my intuition.” I don’t think I can tell the difference between what my gut is telling me and what my pants are telling me. I think that might be 95 percent of my problem???

You seem like a pretty good judge of character based on the cool kids I know you hang out with (not a stalker, you just have public friendships with other people I respect) and based on your choice in a wife. Please help me, Heather Hogan. Otherwise I’m going to have to start letting my mom pick out girlfriends for me. You are my only hope!

Thank you,

I’m The Problem It’s Me

---

Hello, my friend!

This is a good question! I have so much respect for you and this question! I’m going to answer it in a little list — but also, just a small word of warning: Do show some discretion when barreling into new friend groups in a new city looking to date all the people. Queer friends date queer friends, of course, but also be aware that there’s probably like sixteen different webs of past relationships, etc. and it’s better to be cautious than blow up your chance to form awesome new friendships!

With that in mind, here’s ten questions you can ask yourself when you’re hanging out in queer friend groups doing your scouting for red flags. Obviously, someone doesn’t have to meet all these criteria. Also obviously, failing at one or two of them doesn’t make someone a bad guy. This is just sort of a framework to get your brain beans percolating.

I’m wishing you lots of luck and love! By the way, if you love Taylor Swift lyrics and romance, may I suggest Emma R. Alban’s Don’t Want You Like a Best Friend?

love,

Heather

---

1. Do they ask questions and genuinely involve themselves with other people's conversations/stories? 

You can tell so much about someone by seeing if they use group times as a chance to authentically engage with other people, or if they use group times to perform their little one-person shows. And, look, almost everyone on earth loves to talk about themselves, loves a little spotlight, loves the endorphin rush of landing a joke that makes everyone at the table laugh. But is that a piece of the way they interact with everyone, or is it their whole deal?

Do they encourage other people to share things about themselves? Do they find ways to help other people in the group shine? Do they ask questions and show genuine interest in the answers (as opposed to asking questions as a launchpad to share their own opinions, or more stories about themselves)? In my experience, if someone consistently acts like the whole world's a stage for them, that's probably not someone who knows how to experience genuine connection with other humans. 

2. How do they engage with other people's interests? 

Nearly all of my best friends are, in some way, neurodivergent — and that means there's a whole lot of special interests and hyperfixations flying around. I love it. Nothing makes me happier than listening to someone talk animatedly and endlessly about something that makes their heart sing. This isn't what I'm talking about when I say someone who thinks all the world's a stage. There's a huge difference between sharing deep, passionate feelings about a subject and performing the role of yourself to an audience.

When I'm trying to figure out if I'm going to like someone, I can almost always tell by the way they engage with what other people love. Do they mock it, either to their face or behind their back? Red flag! Do they simply wait for the other person to stop sharing about their thing, so they can start talking about themselves again? Red flag! Do they put another person's thing down to make themself feel cool or superior or uplift their own thing? Red flag! I cannot stand being around people who cannot experience joy from other people's joy. 

3. Are they polite to service workers?

If someone's rude to service workers, that's really all you need to know about whether or not they're worth your time. 

4. How do they talk about their exes? 

Of course everyone has complicated feelings about their exes. Hurt, heartache, anger, confusion, disappointment. That's so normal. But if all of their exes are Evil Narcissistic Psycho Monsters, there's a really good chance there's a lack of self-awareness happening there. When I look back on my past romantic relationships, there are obviously things that make me roll my eyeballs about the other people — but there are even more things that make me roll my eyeballs about myself!

Yes, they could have handled X better, but I could have also absolutely handled Y better. Yes, they were kinda clingy, but yes also my deep introversion and need for lots of alone time made them a little insecure, and I could have done a better job reassuring them, rather than getting annoyed, which only made them more clingy. I'm not talking about "Well, I guess my ex was perfect and I'm the worst person in the world" stuff either. I'm talking about a fully realized understanding of both of your contributions to the way things went wrong. I'm talking about the ability to be accountable for your own missteps in your past. The way we talk about our exes is a major tell about our emotional maturity. 

5. Do they know when and how to sincerely apologize? 

I once had a colleague who was so incapable of apologizing that my coworkers and I had to take turns dealing with them when they messed up because none of us could handle it alone or often. "It's your turn to teach them how to be a human today," is what we'd say. You could say to them, "It was really out of line the way you punched me in the mouth last night" and rather than agreeing and saying sorry, they'd immediately start debating you. It wasn't your mouth, it was your nose. It wasn't night, it was afternoon. They didn't punch you, they open-hand slapped you. And they remember one time you saw an open-hand slap on TV and you laughed about it.

Or they're a good person and good people don't punch so there's no way they punched. Or it's your fault they punched. Or, my personal favorite, rather than saying, "I'm sorry I punched you," they'd be like, "Well, I regret not going to the grocery store. I thought about doing that but I went to your house instead and now you're mad." You will never, ever, ever have a healthy and happy relationship with someone who cannot sincerely apologize without prompting or a workshop.  

6. Do they know how to accept an apology? 

If someone's still trying to make you feel bad about something you genuinely apologized and made amends for, weeks or months or years after it happened, get outta there. If they try to "get you back" or punish you, after you've apologized and worked to heal the harm, get outta there. If they are known grudge-holders, like if you see they can't forgive other people, get outta there. It's a tough truth that even the best and kindest people hurt each other sometimes. You have to know how to apologize and you also have to know how to really forgive. Otherwise, you're just having a relationship with a volcano. 

7. Are they constantly taking everything personally? 

There are a lot of tender little lambs in my life, including my wife, but there's a difference between being a little bit sensitive, and constantly reading negativity into situations and inferring criticism and rejection where it doesn't exist. People who take things personally all the time make things about them that have nothing to do with them. Not once or twice, but all the time.

They find it impossible to understand that everyone else is also living a full, complicated life and whatever slight they're seeing is almost always about what the other person has going on at that moment, and nothing to do with them. If a barista is rude to you, it's not because they think you're some kind of worthless imposter punk; they're probably just a little grumpy because being a barista is hard fucking work. If a bartender is slow refilling your drink, it’s not because they think you’re an ugly wanker troll; they’re probably just exhausted because being a bartender is hard fucking work. We're all trapped in our own egocentric predicaments sometimes because that's how our silly little brains are wired, but people who think everyone else's words and actions and behavior are directed specifically at them are really tough to handle in any kind of relationship, especially a romantic one.

8. How do they talk about your friends who aren't around? 

We all know someone who absolutely delights in finding out information about other people and sharing it with anyone who'll listen. That's part of it. The spilling everyone else's business part. But also: How do they talk about your other friends in casual conversation? Are they proud of them? Do they have fun and sweet stories to share about them? Are they excited about this TV show or that book because of your friend who always gives the best recommendations? Did they buy that sweater because they saw your friend wearing it and it looked so good on them? Or, do they use your friends' absence as a chance to be petty and vindictive and mean-spirited? To take little swipes at them? You know as well as I do that they're doing the same thing to you when you're not around.

9. Are they givers or are they get-away-with-ers?

There was this discourse going around the internet a couple of weeks ago about Worst Couples You Know that I think originated on TikTok but I'm not sure. I only use TikTok twice a month to watch videos my friends send me because I still haven't recovered from the time I watched someone just die on there. Anyway, it reminded me of the most miserable couple I have ever met in my life. They seemed really compatible when they first met, and it turns out it's because both of them were the kind of people who love-bombed, and then they lived their entire relationship trying to get away with as much as they could.

Being as mean as they could without the other person leaving, getting as close to cheating as possible without it being "actually cheating" (whatever that means). They were forever trying to get their own way in every situation and it was a constant battle because they both wanted what they wanted way more than they wanted the other person to be happy. Love is at its very best when both people are excited to be generous with the other; it gets you caught in a cycle of giving and gratitude and giving and gratitude.

Here’s a good test for this: If you order a bunch of pizzas for the group, and a person who doesn’t need gluten-free pizza eats the gluten free option just because they want it — when other people actually need it — they’re probably a get-away-with-er.

10. How did their other relationships end?

This is always easy to figure out in queer friend groups because queers are always talking about their exes and are very often each other’s exes. You can use your own personal red flag system to determine whether or not their previous breakups are dealbreakers for you. I wouldn’t date a known cheater, for example. So that’s something I’d be on the lookout for. Also anyone who badmouths cats or Abbott Elementary or Dolly Parton, but that doesn’t usually cause breakups and if it did, go ahead and mark that person down as A MONSTER.