Worthy of a Second Date? Red and Green Flags to Watch For.

By Danielle Andrews

First dates can feel electric or awkward, sparks can fly or fizzle, and sometimes you leave more curious than enchanted. One question looms large after the bill is paid and the final goodbyes are said—should you go out with this person again? With busy lives and other friendships to juggle, deciding whether to invest more time is not always simple. The good news is your first impression holds plenty of clues. By learning to spot the right signs early, you can save yourself future heartbreak or, better yet, make room to discover real connection.

Whether you’re eager for companionship or just dipping your toes in the dating pool, these key green flags can help judge if someone is worthy of a second date. We also point out critical red flags that signal it might be better to walk away. Keep these ten signals close the next time you ask yourself, “Should I see them again?”

When someone shows you who they are, believe them the first time.

Maya Angelou

5 Green Flags That Say Yes!

  • 1. Conversation Flows Naturally

The best first dates often don’t feel forced or like hard work. If your chat drifted from silly stories to thoughtful topics without awkward lulls, that’s a green flag. Genuine curiosity—even if you’re both a bit nervous—is gold. You may find yourselves laughing at the same silly meme reference or genuinely getting lost in conversation about your favorite books. If the words came easily and you never felt judged for your opinions, take note.

“A meaningful connection is as much about good listening as it is about good talking.”

  • 2. Respectful Boundaries and Behaviors

Respect in dating is not optional. Did they wait for you before ordering a drink? Accept “no” gracefully? Were they considerate of personal space and attentive to your comfort? These are not only signs of kindness but of relationship potential. Someone who values your time and boundaries on a first date one is more likely to do so down the line.

  • 3. They Show Authentic Interest in You

Did your date remember details from earlier conversations, or ask about what matters most to you? Whether it’s your work passion project or your recent marathon, genuine interest reveals emotional maturity. If they asked follow-up questions about your hobbies, dreams, or even the little things, you probably left feeling appreciated, not just tolerated. This is the kind of connection that can grow.

  • 4. Shared Values or Life Goals

Opposites can certainly attract, but major misalignments in values or future plans can cause cracks. A green flag is when you spot shared perspectives on topics such as family, career ambitions, travel dreams, or where you want to live. It’s not that you need to agree on everything right away, but feeling some alignment hints at smoother roads ahead.

  • 5. Kindness to Others

How your date treats people who aren’t you speaks volumes. Did they thank the server, hold the door open for a stranger, or leave a good tip? Simple acts of kindness signal empathy and a grounded character. If they go out of their way to be polite and considerate to those around them, it’s not just an act for your benefit.

Kindness is a language which the deaf can hear and the blind can see.

Mark Twain

5 Red Flags Indicating It’s Time to Move On

  • 1. Consistent Rudeness or Disrespect

It’s hard to imagine anyone thinking rude behavior is endearing, but it’s important to be vigilant. If your date poked fun at you in a mean-spirited way, dismissed your opinions, or generally made you feel small, those are significant red flags. The same goes for obvious displays of arrogance or condescension, whether directed at you or others.

  • 2. Only Talks About Themselves

A one-sided conversation quickly grows old. Did your date dominate the exchange, give you little chance to contribute, or seem disinterested in your answers? This pattern suggests they’re not ready to make space for someone else in their life. Healthy beginnings are mutual, not monologues.

  • 3. Dodges Simple Questions or Is Vague

Openness fosters trust. If your date avoided straightforward questions about their life, job, or interests, or if their answers seemed evasive, beware. Transparency doesn’t mean unloading your entire life story in one sitting, but basic honesty is a must. Evasions this early rarely bode well.

  • 4. Disregards Your Boundaries

Whether it’s pushing for another drink when you’re done or making inappropriate jokes despite your discomfort, ignoring boundaries is a major red flag. Your first impression of someone’s respect for your limits is often the most accurate one you’ll get. Honor your feelings and keep your standards high.

  • 5. All Negativity, All the Time

Everyone has a hard week, but if your date’s conversation was laced with complaints, bitterness about exes, or cynicism about life in general, that’s a warning sign. Positivity is magnetic, and constant negativity drains energy. Look for someone who can rise above setbacks and finds reasons to laugh, even on Mondays.

Surround yourself with only people who are going to lift you higher.

Oprah Winfrey

In Psychology Today Magazine, Clinical and Forensic Pyschologist Ahona Guha offers helpful advice in her article, 6 Potential Red Flags in a New Relationship .

Listening to Your Gut Will Always Be in Style

Deciding whether to see someone again can be nerve-wracking, but your intuition is your best guide. Pay attention to how you felt during and after the encounter. Did you leave energized and optimistic, or anxious and doubtful? The biggest sign of all might be how you feel about yourself in their company.

One of the best advantages of signing up with Kelleher International is the coaching we provide to help with first date jitters to make sure everything goes smoothly and your first date is a success. These are the kinds of things we will discuss with you about how to approach your first date and then help you unpack how it all went.

If you spot more green flags than red, you might just be on your way to a promising connection worth building on. But if warning bells are ringing, grant yourself permission to say “No, thank you” and move forward in search of something that feels genuinely good.

Dating is as much about discovering what you want as it is about finding someone who meets your standards. Protect your peace, trust your instincts, and stay open to the possibility that amazing people can still surprise you.

Of course if you’re still looking for that special someone to share your life with, don’t put it off one more second! Contact us and allow our talented matchmakers to get to work on your behalf.