The Relationship Red Flags Holly Madison Wishes Every Woman Recognized Sooner

TikTok can tell you how quickly someone should text back and how much they should spend on dinner—but Holly Madison thinks those rules may be making dating harder, not safer.

On Tell Me I’m a Good Mom, Madison joins Lo Bosworth to share the relationship lessons she had to learn the hard way. No, she doesn’t think women should lower their standards; she just wants them to stop confusing surface-level dating behaviors with meaningful signs of whether a relationship is healthy.

Madison warns that the “crazy unrealistic expectations” circulating online could “drive people toward loneliness.” Her advice makes a strong case for retiring the arbitrary dating rules and getting much clearer about the red flags that deserve our attention.

Holly Madison on Online Dating Rules and Red Flags

You should be able to ask for what you want

Women are often encouraged to keep their expectations quiet, play it cool, and wait for the other person to decide where things are going. Madison thinks the idea that expressing what you want will “scare a guy off” is BS. Staying silent may feel like a way to protect the relationship, but it also leaves you hoping someone will eventually figure out what you need without being told. Meanwhile, you’re learning to make yourself smaller just to keep their interest.

Sure, being direct may not always get you the answer you hoped for, but it gives you useful information. If someone loses interest because you voiced a reasonable need or asked where the relationship was headed, the question did not ruin a promising connection. 

If you’re hiding his behavior from your friends, pay attention

Sometimes the biggest red flag is the part of your relationship you keep editing out in conversation. You may not be ready to call the behavior wrong, but if you feel embarrassed to tell the people you trust what happened, that discomfort is worth examining.

“I think the best piece of advice I’ve heard as far as like, do you know if this guy’s doing you wrong or not, is if you have something going on in your relationship that you’re embarrassed to tell your friends about,” she says.

Of course, not every friend gives fair or helpful advice. Madison makes an exception for the “crazy toxic friend who’s just trying to sh*t on you.” But when you find yourself hiding the truth from the reasonable people who love you, that is different. That embarrassment may be telling you something you are not quite ready to say out loud.

Love bombing can look like pressure, not just affection

Love bombing is often pictured as a flood of compliments, gifts, and attention. But there’s another version that can be easier to mistake for commitment: someone trying to move the relationship forward much faster than you want.

Madison describes it as being pressured into major relationship milestones “long before you feel ready.” From the outside, that urgency may look romantic. A person seems certain about you, talks seriously about the future, and wants to make things official. But their enthusiasm does not cancel out your discomfort.

Ask yourself this: Are you still allowed to have a say in the pace? Genuine affection leaves room for you to slow down, ask questions, or say you are not ready without being made to feel guilty. Pressure treats your hesitation like a problem that needs to be overcome.

Isolation is not the same thing as protection

Controlling behavior in a partner can sneak up on you. They position themselves as the person who values you most, then use that supposed devotion to make you question the intentions of everyone else. 

“They will meet your friends or your family, and they try to act like their opinion of you is so high, and they’re just looking out for you,” Madison says. “They try to act like they don’t like your friends, like those people aren’t good enough for you, or they’re using you, or that’s kind of how they frame it, and you know that’s not true, like you feel it in your heart, but they’re really pushing that.”

Over time, seeing the people you love may begin to feel like more trouble than it is worth—not because those relationships changed, but because your partner has made maintaining them so uncomfortable. “And it gets to the point where you don’t feel comfortable bringing your friends around, or you know if you tell your significant other you’re going to go see your friends, you’re just going to get sh*t on,” Madison says. If their “concern” leaves you with fewer people to turn to, pay attention to what that concern is costing you.

To hear Holly Madison’s full conversation with Lo Bosworth, listen to Tell Me I’m a Good Mom wherever you get your podcasts.

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