8 Covert First-Date Red Flags You Should Not Ignore

Dating and relationships are inseparable from each other. Dating is not just a “phase” of the relationship. It’s the foundation.

Whatever habits you notice when dating someone is what you can expect in a serious, long-term relationship.

As soon as that first date happens, no matter how long you’ve known someone, you have entered a “shared” relationship.

I’m going to share this short excerpt from the book, Dating Sucks, but You Don’t, by Connell Barrett.

In chapter eight, he describes the fundamentals for “great first dates.” Like anything meant to last a long time, you have to gradually build a strong foundation. Basically, you work your way from the bottom up.

Whether that’s a first date or a long-term relationship, none of these red flags you’re going to read about have any place in such an interaction.

“The Triangle of Connection”

This is what he coined in chapter eight.

“A great first date is when two people go from being relative strangers to feeling a strong romantic bond…Picture yourself and the woman inside a triangle. And imagine that the triangle consists of three levels. You both begin at the base, on the bottom level and on opposite sides. As time passes, you “escalate” together toward the top, the two of you getting closer and closer.”

You start with “small talk,” and work your way up to deeper, more personal, and emotional communication. And at the last stage, the goal is to interact as if you are a couple (even if it’s the first date).

This “triangle” is critical, because all of these red flags seriously disrupt the natural flow or escalation of this behavior.

1. Flaking, tardiness, or trouble with planning dates

A lot of people make excuses.

And it’s really easy to rationalize or enable poor behavior.

I’d have girls show up late, and especially when I had them flake, I would rationalize it by thinking

Oh, she probably is just busy, it’s fine. It’s not that big of a deal. It’s okay, we can reschedule.

I’ve accepted ghosting or “flakiness” as “just how they are” instead of seeing it as blatant disrespect for my time.

For example, I had a date planned and at the last minute, I was given some weird excuse that she had something going on with school (on a Friday night). The story is more convoluted than that, but I ignored the red flags and gave her the benefit of the doubt.

But nothing came of that. We never met up.

Being late or inconsistent will simply carry over into the relationship itself. Why would someone value you or your time if they’re showing up late or not at all on the first few dates?

Nothing will change. It’s not like they’ll change their mind later on and make exceptions for you.

2. Habitual complaining or negativity on a night out

Complaining can be a way to build common ground or build trust. It makes sense that complaining or venting your problems to a significant other can be okay.

You know each other and it helps to find wisdom or solace in your “person.”

But on a first date… that’s a different story.

As mentioned earlier, if you want to actually build something real with someone, you have to create a strong foundation first.

When you try to skip ahead, it creates problems. And complaining doesn’t help at all.

Here’s why.

At the very start of the date, you should try to focus on fun, light-hearted topics. You know, interests, hobbies, or experiences. That sort of thing.

Complaining about a shared dislike of something might fill in the space, but negativity usually just begets more negativity.

And yes, venting might jump-start a conversation to a more intimate, deeper one, but usually, it just derails emotional intimacy with another person. Plus the other person will get overwhelmed or turned off by it.

It’s not attractive. And it raises a lot of questions.

A perfect example is on a first date I had with some girl, one of the first things she talked about — or rather complained about was her ex.

Which we’ll get to very shortly. Why that’s a huge issue too, but instead of warming up to the date like a normal person, I was suddenly listening to the story about her crazy ex.

In short, it was very jarring. It just didn’t feel right.

Rather than having fun and sharing a nice moment, I was put off by her attitude. I had to pretend to be interested and sympathetic, and the date itself did not go as well as I wanted.

What’s worse is I continued to date her!

And she often dragged our conversations into the realm of negativity. Shocker, huh?

I just didn’t feel much of a connection to her, mostly because of that.

3. The random phantom ex that showed up

While it’s pretty “mainstream” that those who talk about their exes straight out the gate are walking red flags, it’s so easy to get caught up in the moment.

When that girl brought up her ex (and it wasn’t the only time), you may find yourself feeling sympathy for someone who had a terrible partner.

So you tend to gloss over it as a red flag.

But it’s a huge one.

Talking about past lovers on the first few dates kills any connection. Yeah, it’s good to talk about past relationships eventually, but not in the first few minutes.

Remember the “Triangle of Connection?”

Exes severely interrupt this delicate process. And it also shows they’re emotionally entangled with someone else and possibly a person who avoids accountability.

If one complains too much about an ex with your dating partner, it’s annoying and demonstrates a severe lack of personal accountability for the role they played in their last relationship.

And if they didn’t take responsibility then, why would they when they are in a relationship with you?

Because people rarely change. Not unless they have a burning desire and intention to change. If avoiding problems and blaming their ex has gotten them “this far,” there’s no motivation to change, grow, or heal.

4. Their cellphone is more important than you

I’m gonna keep this one short and sweet because it’s more of a personal pet peeve, but still rather destructive.

I get immediately turned off when a girl checks her phone or her smartwatch on a date. Makes me uneasy. It signals to me that the conversation isn’t worth her full attention.

Because to me, I’ve set aside time out of my day to invest a few hours with someone I don’t know. I mean, who knows how the date might go?

Maybe it’s a total flop and now I’ve wasted a few hours and probably a few bucks on a chick who thinks her Instagram account is more important.

Or that random text from her friend.

It’s really simple. It’s distracting and disrespectful.

I understand that phones are addictive, but if you can’t put your phone away for a few hours on a date, what’s going to happen when it’s time for an important discussion?

It wouldn’t be wrong for me to say men often feel starved for an emotional connection from a woman. We care more about the emotional connection than most people might realize. It’s not just sex we want. And a woman’s full attention is highly attractive and irresistible to a guy.

When that phone gets pulled out…total mood killer.

If we can’t connect at the moment, how in the world is that supposed to happen later on?

5. They dump all their baggage on the first date

This is a tricky thing to unpack. Because the lines can get blurred between vulnerability and trauma dumping.

With trauma dumping, I’ve noticed there’s not much awareness for the other person. On one date, this girl unloaded her life story within about an hour’s time frame.

Without much regard for interest in who I was as a person.

Even before this, I was in a short-term situationship in which we practiced trauma dumping. She poured out her heart and soul to me. And I felt like her therapist or her father.

Yet, simultaneously, I felt sympathy for her, and it was like a twisted version of love.

It’s great to be an empathetic listener and get to know someone fully who you intend to date, but unloading all your emotional baggage all at once is extremely overwhelming.

It seems like it’s done for a couple of reasons.

People treat dating as a means to “not be lonely,” but they don’t take into account that they’re engaging with another HUMAN being. It’s all about them. If they can find someone to listen to all their problems and get a free drink out of it, even better. Which is why I sometimes joke with people I know I should have charged some girls for my time. If I’m gonna play therapist, why not get paid for it?
Some people are moderately or severely avoidant. Meaning they cannot handle their own emotions or feelings. Or rather they’d prefer to avoid even dealing with their problems. They’re afraid of real intimacy, but they still crave love and affection. And this is just what I’ve noticed, but “trauma dumping” seems to serve as a way to connect artificially or superficially without actually being real. On a date with someone who trauma dumps, it might seem like a real connection, but it’s completely fake and short-lived.

It doesn’t matter what the reason is, trauma dumping is quite deceiving, and it completely misses the mark when it comes to actual connection.

Plus, as I’ve personally experienced, it tends to compel one to want to “fix” the partner.

I went out of my way to provide emotional support or comfort to some of these girls who would have never been, in a million years, interested nor capable of reciprocating that same comfort to me in a tough time.

So don’t get caught up in trying to be a “fixer” or an open door to someone you just met.

6. A very noticeable lack of “we” or “us”

If you can remember from earlier, the last step in the “Triangle of Connection” is a feeling of “us as a couple.”

On the first date, you should look out for signs that the person sitting next to you is beginning to use language that suggests a mutual connection.

It doesn’t mean that they have to be totally in love with you or infatuated with the idea of “we” or “us,” but just look for subtleties. Maybe it could just be “Hey, we should go get drinks after this.”

Or, “I’d like for us to go on another date.”

The specifics are irrelevant.

Do you get the feeling they’re interested in a future “we” or “us.”

While this isn’t a hard and fast rule, an emotionally available person is more likely to be willing to include you in things to gauge where the relationship is headed.

Whereas, emotionally absent people tend to be interested in only themselves and what serves them.

But don’t get these two things confused. If you haven’t gotten to the “we” step in the romantic triangle yet, it doesn’t mean an automatic red flag.

It might just take more time to build a connection.

Yet, I’ve been there. In those kinds of situationships that lasted for weeks or months, there was a complete lack of “we” and “us.” It felt like a complete free-for-all.

Not a shred of commitment, or interest. Nothing. Just two “single” people dating and having sex.

7. You wonder if you’re being interrogated by police

One time I was on this date that seemed like an interrogation. It was like a back-and-forth Q & A session.

I’d ask her what music she liked. And she would do the same. Then we’d switch topics. To be fair, it was the first date I had been on in many years after the end of one relationship, so I was quite rusty.

But… I got bored of that. Stood up, told her I was ready to go and we walked out. I never spoke to her again. That’s not necessarily all her fault, nor is it a red flag by itself, because some people just don’t “click” and then things feel weird or forced.

I get that it takes two people to form a relationship. And ultimately the success of said bond is the responsibility of both people, but if you’re experiencing extremes, it’s time to seriously reconsider the date.

You should ask questions, but when it becomes excessive right at the beginning, that person is probably experiencing some kind of insecurity.

I’ve seen it mostly in those who I would categorize with a fearful avoidant attachment style. They’re extremely afraid of getting hurt, so they want to “know everything” about you before deciding that they can feel safe.

Then, on the other hand, you have the minimalist. The dismissive-avoidant types. They won’t ask you any questions AT ALL.

They pull out their phone, and play a game while you ask them about their day, or what they’re interested in and they give you short answers. And all of these examples are things I have experienced. I’ve seen A LOT of it.

Then you wonder, “Damn, am I seriously not that interesting??”

I don’t think I need to go on too much about how a conversation needs a natural ebb and flow.

8. “I don’t want to waste my time or yours”

This might be a very specific red flag, but on occasion, you’re bound to hear it.

I’ve grown to seriously dislike this phrase.

Because people who use this phrase WILL absolutely waste your time.

This phrase might be part of this question:

“What are you looking for? I just need to know so I don’t waste my time and yours?”

I know it makes sense to figure out someone’s dating intentions, but throwing in that phrase makes it seem demanding or disingenuous.

It seems like they might be judging or calculating whether you fit their strict criteria.

If you don’t meet their “initial” standards without getting to know you a little bit at first, you’re not even worth their time and day.

Generally, just seems more transactional than anything else. And on a more fundamental level, they might not feel the need to communicate an issue, because to that person, if their standards are so rigid, why would they bother to tell you if they have a problem?

If you don’t “check” one of their boxes, it’s time to go.

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If you can remember one thing, listen to your gut

You just read about “not wasting time,” and how that phrase can be an early warning sign, but recognizing red flags is crucial to not wasting time.

Would you rather waste your time with the wrong people or be able to know when to walk away?

I’d rather walk away when it’s necessary.

But the choice is yours, you can choose to date individuals who aren’t fully committed, or you can choose people who are safe and emotionally available.

If there’s one thing you should remember, it’s the “Triangle of Connection.”

You start out as acquaintances. Then you move on to friends, and ultimately as lovers and partners.

Anything that interrupts or halts this natural flow is NOT good. So next time you’re out on a date try to recognize any of these red flags. If you spot any, take the time to think about the interaction afterward.

And if you did not notice any, that’s even better.

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