The 9 Biggest Red Flags on a First Date with a Guy

First dates can be exciting, nerve-wracking, and full of possibility. But they’re also your chance to spot the biggest red flags in a guy before you get too invested.

We’ve all been there…sitting across from someone, feeling that odd sensation in our stomach that something isn’t right. Those instincts are trying to protect you and shouldn’t be ignored.

We’ve helped many good women navigate the dating world. Over the years, our love and relationship experts have seen how missing some warning signs early on leads to heartache down the road.

Many say they wish they’d paid closer attention on that first date.

We believe every woman deserves a healthy relationship. Looking for these red flags isn’t about being too picky…that’ll prevent you from attracting love into your life.

It’s all about protecting your heart, well-being, and future.

Major First Date Red Flags in a Guy You Shouldn’t Ignore

The excitement of meeting someone new can easily cloud our judgment. As a result, while wondering if he likes you after the first date, you may overlook behaviors that normally set off alarm bells.

Let’s explore the warning signs that should make you think twice before scheduling that second date.

1. He Doesn’t Respect Your Personal Space

Personal space violations are among the most telling red flags on a first date. If you dismiss these early warning signs, you may find yourself in a relationship where boundaries are regularly crossed.

We are talking about him sitting unnecessarily close, touching you without permission, or leaning in too far when speaking.

When considering someone a healthy partner, you’d expect them to understand and respect physical boundaries, especially before comfort levels are established.

Some men might brush off your discomfort with statements like “You’re too uptight” or “I’m just being friendly.” These responses are concerning because they prioritize their desires over your comfort.

Trust your body’s reaction in these moments.

That uneasiness you feel isn’t an overreaction, but your intuition signaling that something’s wrong. A good man worth holding onto will naturally give you space, allowing the connection to develop at a pace that works for both of you.

2. Controlling Behavior Appears Early On

We remember Lisa, a 42-year-old, very good-looking woman whom we had been helping to find true love again. She called us after a particularly frustrating dating experience.

Her date had ordered for her without asking what she wanted, repeatedly checked her phone when it buzzed, and insisted on changing their plans midway through the evening despite her objections.

If you ever encounter a date who dictates where you sit, what you eat, or how long you stay somewhere. A man you barely know who criticizes your choices or offers “suggestions” about your appearance that feel more like demands…that’s an obvious red flag.

He attempts to establish dominance in the relationship dynamic.

What makes such behavior particularly dangerous is how it escalates over time. The man who insists on choosing your meal on a first date may later try to choose your friends or career path.

Early controlling behaviors will certainly lead to more serious forms of emotional abuse down the line.

So, when you sense that someone is trying to manage your decisions rather than share an experience with you…it’s best to thank them for the evening and move on.

3. He Treats Wait Staff and Service People Poorly

How someone treats people they perceive as having less power speaks volumes about their character. We consistently find this behavior to be one of the most reliable predictors of how someone will eventually treat you in a relationship.

One particular client, Meredith, shared how she ignored this warning sign with a charming executive who seemed perfect until their first dinner out. He snapped at their waiter for a minor mistake, demanded special treatment, and left no tip.

While she felt that new relationship anxiety, Meredith thought her date was having a “bad day.” Within a few months, that same impatience and disrespect were directed at her.

Notice if your date speaks condescendingly or becomes disproportionately angry over small inconveniences. These behaviors reflect how they handle frustration and how they view people they don’t need to impress.

Someone who shows basic kindness and respect to everyone demonstrates emotional intelligence and compassion. You should seek these qualities before considering building a relationship with a man.

Someone who can’t manage basic courtesy during what should be their best behavior (a first date) will likely show much worse once they’re comfortable.

4. Backhanded Compliments That Create Self-Doubt

Compliments should make you feel appreciated, right? Not confused or slightly hurt.

It’s easy to miss these veiled insults delivered with a smile, but they’re another major red flag in guys. Especially when they plant seeds of self-doubt while providing plausible deniability…”I was just giving you a compliment!”

Some examples of backhanded compliments to watch out for:

“You’re actually pretty smart for someone so beautiful.”

“I don’t usually date women your size, but you carry it well.”

“That outfit is so brave—I could never pull that off.”

“You’re more interesting than your social media made you seem.”

“Your job sounds so easy and fun compared to what I do.”

“It’s refreshing to meet someone who doesn’t try too hard with makeup.”

“You’re pretty articulate for someone who didn’t finish college.”

Do you see how these statements contain an implied criticism wrapped in praise?

A man who uses these tactics tests your response to his criticism and your willingness to seek his approval. He is certainly not the type of man you want to show your feminine side.

5. He Doesn’t Show Genuine Interest in Your Stories

Conversation on a first date should feel balanced, with both people asking questions and actively listening. If you spend an entire date interviewing a guy while sharing little about yourself…that’s an obvious red flag.

When you do get a chance to speak, notice whether he maintains eye contact, asks follow-up questions, or quickly redirects the conversation back to himself.

We’ll illustrate this by quoting one of our clients, Jackie. Here is how she described a date with a successful businessman who seemed perfect on paper:

“Every time I started talking about my work or interests, he’d listen for maybe thirty seconds before finding a way to steer the conversation back to his accomplishments. I felt like I was sitting across from a resume, not a person interested in knowing me.”

This isn’t just about poor social skills. It suggests that the guy will struggle to see you as an equal partner with valuable thoughts and experiences, which leads to an unhealthy relationship.

6. Love Bombing and Overwhelming Affection

Love bombing feels amazing at first. It’s like all your romantic dreams coming true at once.

Excessive compliments, declarations of strong feelings, talk of future plans, and lavish attention or gifts…all on or immediately after a first date.

While it seems wonderful to be so desired, we’ve witnessed how this behavior often masks concerning intentions. As Maya Angelou says:

“When someone shows you who they are, believe them the first time. If it seems too good to be true, it usually is.”

This wisdom applies perfectly to love bombing situations. You might meet someone who calls you “the one” before dessert arrives, texts constantly after your date, or makes grand romantic gestures that feel disproportionate to your brief connection.

The problem with love bombing is that it’s typically not sustainable or genuine. It creates a false sense of intimacy before real trust is established. Guys often use this technique to secure emotional attachment before their red flags become obvious.

Once they feel you’re invested, the excessive affection frequently transforms into manipulation, control, or emotional withdrawal. And these aren’t the love ingredients for lasting relationships.

7. Constant Talk About Ex-Partners & Toxic Relationships

When a first date turns into a detailed history of past relationships, we say it’s a warning sign. You deserve a man present with you, not mentally entangled with their exes.

There’s a big difference between briefly mentioning other relationships when relevant and dominating the conversation with stories about “crazy exes” or unresolved grievances.

Pay attention to both the frequency and tone of these references.

A guy who describes all previous partners as “psycho,” “controlling,” or “impossible to please” is telling you something important about himself…not his exes.

He probably never tried dealing with relationship differences and places all the blame on others.

Similarly concerning is the date who seems obsessed with one particular ex, whether through constant comparisons or bringing her up in unrelated conversations.

If your date seems fixated on past relationships (especially in negative ways), it indicates unresolved feelings and potential emotional unavailability.

8. He Shows Signs of Substance Abuse Issues

We’ve worked with women involved with guys whose substance use caused chaos in their lives. Motivating a man is no easy task…and it gets really hard if he has lost his way.

You don’t want that. Nothing wrong with having a drink or two on a date, but there are concerning behaviors you should watch for.

Notice if your date seems unable to enjoy themselves without alcohol or other substances.

Do they seem anxious until they’ve had a drink?

Do they pressure you to drink more than you want?

A particularly concerning sign is when someone’s personality shifts dramatically. He becomes more aggressive, overly emotional, or displays poor judgment, to give you a few examples.

Other red flags include frequent trips to the restroom, excessive spending on drinks, or a defensive attitude about their consumption.

Substance abuse issues impact much more than just the individual using. They affect a relationship’s financial stability, emotional well-being, reliability, and safety.

9. Your Core Values Are Completely Misaligned

Perhaps the most fundamental red flag of all isn’t about behavior but about essence…who you both are at your core. Now is the perfect time to quote Susan David:

“Your core values are the compass that keeps you moving in the right direction.”

We also believe this deserves serious attention. Core values aren’t preferences, but rather the guiding principles that shape life’s most important decisions. You might feel attraction and chemistry, but when core values clash, relationships face tremendous strain over time.

This misalignment reveals itself in first-date conversations about family, politics, money, religion, or future goals.

It appears when you mention valuing independence, and he jokes about women always needing guidance.

It surfaces when you discuss career ambitions, and he dismisses them as a temporary thing until you “settle down.”

It emerges in comments about children, lifestyle choices, or how he speaks about different communities.

After so many years of providing love and relationship guidance, we know that true compatibility doesn’t require identical views on everything. However, mutual respect is needed for each other’s core beliefs and similar visions for life’s most significant aspects.

When values align, you have a solid foundation for building true love in a relationship.

Trust Your Intuition When It Matters the Most

Reading an article about the biggest red flags in a guy may leave you confused about what to expect from men. It may seem like dating is just about avoiding the wrong people.

It sure isn’t…but it’s better to create space for the right ones to enter your life. Every date that doesn’t go well brings you one step closer to one that will.

The most powerful tool you possess as a woman is your intuition.

That quiet voice inside that whispers “something isn’t right” deserves to be heard. Too often, we talk ourselves out of these instincts, making excuses for behavior that makes us feel unsafe or unvalued.

Are you noticing warning signs in someone you’ve recently met?

Or maybe a guy you just dated showed too many green flags?

We understand these uncertainties and are here to help you sort through them. A brief psychic reading over the phone with one of our love experts may be exactly what you need.

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