The Second-Date Dilemma: How to Know If You Should Say Yes

Updated: Jun. 05, 2024

Just because you weren’t head-over-heels after the first date, it doesn’t mean you should rule out a second date. Here are the signs that a relationship might still be in the cards.

Congratulations—you survived the first date! Not only did you plan the perfect outing, but you also received a nice compliment or two and blushed as you exchanged flirtatious jokes. But right when things started to look promising, your date took a work call in the middle of dinner or the conversation faded into awkward silence. Now you’re not so sure if a second date will be worth it. I’m here to tell you that it just might be, despite those disappointing bumps in the road.

As a therapist who specializes in relationships, my job is to help people filter out bad matches and find healthy long-term relationships. Of course, you’re not alone if you struggle to decide whether to accept or ask for another date—or if you accidentally end a potentially amazing relationship before it even starts. Yes, you read that right. As long as the other person isn’t exhibiting any serious red flags, you might want to give them another chance. The key is identifying certain “yellow flags” before making your decision.

While I have been down this road with many clients over the years, I also consulted psychotherapist Tasha Bailey, author of Real Talk: Lessons from Therapy on Healing & Self-Love, to get her perspective. Together, we will help you navigate a few typical issues you might encounter on a first date—and decide whether you should see where things go on a second.

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About the experts

  • Gloria Zhang is a therapist and relationships coach based in Canada. Her signature course, Situationship to Soulmate, helps women transition from toxic relationships to secure, lasting love. She is also the author of A Woman’s Guide to Inner Child Healing and the host of The Inner Child Podcast.
  • Tasha Bailey is a U.K.-based psychotherapist who has more than seven years of experience specializing in trauma, self-love and creativity in therapy. She is the author of Real Talk: Lessons from Therapy on Healing & Self-Love.

Why you should consider a second date

Most people feel nervous on the first date and don’t get a chance to fully shine. Admit it: You’ve been there too! Maybe you fumbled over an easy question, had spinach stuck in your teeth all night or accidentally laughed when your date started telling a sad story about their grandma. It’s also common for people to tell you what you want to hear instead of reveal their honest opinions.

While first dates are more for breaking the ice and getting the initial small talk out of the way, second dates often go deeper. You’ll also be a lot more relaxed during them. And that’s a good thing because that second date will help you figure out if your suitor is well suited for you, as well as truly ready for a relationship or just looking for a fling. “Vulnerability and emotional openness can be a great sign of someone’s emotional availability,” says Bailey. But you usually have to get to the second date (or beyond) to figure that out!

Yellow flags for a second date

How do you know if a potential relationship is worth exploring? Think back to your first date. Green flags are generally pretty clear, but the following yellow flags can be confusing. Here’s what you should keep in mind about them and why they could equal a “yes” for a second date.

Your first date was “good”

couple hugging good bye after a good date with a yellow flag icon in he bottom left cornerRD.com, getty images

Sure, “great” would be better, but “good” is, well, probably good enough to warrant a second date. Remember: Accepting a second date with someone doesn’t mean you’re locking yourself into a relationship—it just means you’re giving the other person a little more consideration. Your first date just needs to be pleasant, not perfect. So don’t write off someone just because they accidentally dropped a spoonful of dessert or made one lame joke.

Many of my clients grew up with Hollywood movies and have unrealistic expectations of how a first date should feel. Yes, it would be dreamy to reenact The Notebook and ride off into the sunset with Ryan Gosling. But in reality, it can take multiple conversations to really get to know someone (even Ryan Gosling). As long as you had fun and felt comfortable, it may be worth a second chance to explore further.

You didn’t feel a spark

I hear this a lot: The date went great except for one thing—there were no fireworks. As a result, you might be tempted to cut things off right then and there. After all, why waste your time (and the other person’s time) if you didn’t feel that connection? But here’s the thing: In my work, I’ve found that sometimes it can take five to eight dates to begin feeling a romantic attraction to somebody. True love takes time because it is built on a solid foundation of trust and friendship. This is why so many friends end up in relationships with each other. You could be tempted to speed up the process especially if you’re older so here are a few tips for finding the right person if you’re dating in your 40s. Don’t worry if your first or even second date isn’t electric. If you enjoy spending time together, why not see where it goes?

It’s also common to confuse healthy chemistry with toxic highs and lows. A healthy spark is consistent and warm like a steady fireplace, whereas an unhealthy spark is disruptive like a firecracker and burns out just as quickly. The problem with intense relationships is that the roller coaster of emotions can distract us from noticing red flags. Though exciting, intense flames alone don’t provide the foundation for a healthy, lasting relationship.

They have a weird sense of humor

man and woman laughing on a date with a yellow flag icon in he bottom left cornerRD.com, getty images

Maybe he laid heavily into the dad jokes or really needs to work on his comedic timing. Or maybe her attempts at breezy humor fell flat. Though first-date jokes can feel cringey, they are hardly representative of someone’s full potential to make you laugh for life. In fact, after my first date with my husband, he thought it would be hilarious to send me custom meme images based on things he remembered about me. Some people might have found it a little childish, but I chose to look at it as endearing! Years later, his funny bone has greatly evolved.

The truth is, it’s normal to make terrible or even inappropriate jokes when we’re nervous. And while we all want a partner who can make us crack up and feel all warm and fuzzy, why not see if you can learn to appreciate their unique sense of humor? Those odd quirks may turn into endearing charms over time. That’s why you shouldn’t judge a book by its cover—or in this case, by the first joke.

You’re both looking for the same thing

Did you discover on the first date that you’re both seeking a serious relationship—or just looking to have fun? You’d be surprised by how many people avoid asking this question early on. But being clear on what you’re looking for will prevent wasting time with someone who isn’t a match. Someone who is on the same page as you will most likely share the same goals that you have. Plus, you could spend the second date learning more about their expectations for an ideal relationship and what they’re looking for right now.

Your conversation flowed well

two men drinking wine and having a nice date with a yellow flag icon in he bottom left cornerRD.com, getty images

There’s nothing more satisfying than a buttery-smooth conversation on a first date. If you laughed at each other’s jokes and bounced ideas back and forth, then it’s a sign that you have similar communication styles. Accepting a second date will help you determine if this compatibility will extend to more serious topics too. And no, the conversation doesn’t have to be perfect—let’s not forget about those nerves!—but for you to agree to a second date, some degree of conversational comfort is necessary.

Red flags to watch out for

On the flip side, some behaviors should elicit an automatic “no” for a second date, because they reveal undesirable characteristics about your date. Here are five red flags you need to be aware of, based on my professional experience.

They don’t respect your boundaries

woman sitting close to a man on a date showing him something on her phone with a red flag icon in he bottom left cornerRD.com, getty images

Someone who ignores your personal boundaries is disrespectful, and this behavior can indicate future boundary violations. What might this look like on a first date? It could be something seemingly innocent, like repeatedly bringing up topics you’ve made clear you don’t want to discuss, or something more uncomfortable, like continuing to make physical advances after you’ve expressed your discomfort. “When it crosses the line without our permission, it shows a disregard for emotional boundaries,” says Bailey.

If you say no or change the subject, that should be the end of it. And by the way, it’s not an excuse if they’ve had some wine to drink.

They’re rude

If your date is being rude to you or the people around you, a second date should not be on the table. If they’re already rude on the first date when they should be making a good impression, it can leave you imagining what an entire relationship would feel like—and you’d probably be right. My client “Kevin” was having a pleasant dinner out until his date began barking orders at the waiter. Kevin realized that he didn’t want to risk being on receiving end of that behavior. Snarky or demeaning behavior with anyone is an indication that your date may have a sense of superiority and may treat you just as poorly later on.

They keep bringing up their ex

two men on a date sitting on a bench and one is complaining about their ex, with a red flag icon in he bottom left cornerRD.com, getty images

If your date repeatedly brings up their ex-partner, it could be a sign that they’re not over them yet. A date should feel fun, not like a therapy session. It’s an even worse red flag if they keep speaking negatively about their ex. “A hard pass would be if they speak about these people disrespectfully or mockingly, such as labeling an ex-partner as ‘crazy,'” says Bailey. “This shows their lack of accountability for their past relationships, which could then reflect the lack of accountability they would take in a relationship with you.”

They “neg” you

“Negging” is dating slang for a manipulative way of giving backhanded compliments, with the hopes that you will feel insecure. People who use shady strategies like this tend to struggle with communicating their feelings openly, but overall, when someone is that eager to chip away at your self-confidence, you could be looking at the start of an unhealthy relationship. My client “Emily” was once told on a first date, “I see your potbelly—you look like a cute little snowman.” If your date resorts to cheap tactics like this, it’s a sign that they play mind games.

They don’t show a true interest in getting to know you

man talking a lot during a dinner date with a red flag icon in he bottom left cornerRD.com, getty images

Sometimes people ramble on about themselves because they’re nervous about being on a first date. However, if your date seems unable to show interest or ask you questions about yourself, it can be a red flag about their ability to be attentive in a relationship. Or, at worst, it could be a sign of narcissistic behavior, which is another big problem. You can tell this is an issue if you feel like you’re being talked at, instead of talked with.

What should your date be doing? Asking you about your values and interests, looking for common interests, getting curious about your answers and listening when you speak.

The bottom line

A second date is just a second chance to get to know more about the other person. As long as you feel safe, have a connection and don’t observe any major red flags, it just might be worth it. Overall, though, trust your own inner voice and listen to your feelings when making dating decisions. The right person—for a second date and beyond—will make you feel heard, safe and respected.

Why trust us

For over 100 years, Reader’s Digest has explored the nuances of relationships, working with such luminaries as Dr. Ruth Westheimer, John Gottman, PhD, and Leo Buscaglia (“Dr. Love”). We ran a decade-long relationships column and published a compendium of features, Love and Marriage: The Reader’s Digest Guide to Intimate Relationships. For this piece on second dates, Gloria Zhang, author of A Woman’s Guide to Inner Child Healing, tapped her experience as a psychotherapist and relationships coach. Then, clinical psychologist and life-fulfillment expert Carla Marie Manly, PhD, author of The Joy of Imperfect Love and Date Smart, gave it a rigorous review to ensure that all information is accurate and offers the best possible advice to readers. We support this information with credentialed experts and primary sources such as government and professional organizations, peer-reviewed journals and our writers’ personal experience where it enhances the topic. We verify all facts and data and revisit them over time to ensure they remain accurate and up to date. Read more about our team, our contributors and our editorial policies.

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