Biggest Mistakes That Ruin a Second Date
If you are new here, first read about first date mistakes here.
If you made it past the first date—congrats! This is no small feat in this day and age. It's hard to sift through the haystack and find any shiny needles!
I assume there was enough chemistry on date number 1 to make you want to give it a whirl a second time, and you’re excited to see where this could lead. But don’t get too comfortable.
The second date has its pitfalls and landmines, just like the first one! If you make the mistakes I am about to reveal, you might send the wrong message about how serious you are, slow down the process, or even blow it on a good potential connection.
The bottom line? If you want the opportunity to turn this into a real relationship, you need to avoid these common mistakes:
1. Choosing the Wrong Setting – Don’t Let Distractions Ruin a Good Time
One of the biggest second-date mistakes is choosing an environment that doesn’t allow you to focus on each other. Loud restaurants, concerts, or crowded parties might sound fun, or less stressful than staring at each other face to face for hours, but the inherent distractions prevent the kind of questions and answers to which you need to attend.
The best way to set yourself up for success is by choosing a quiet, cozy setting where you can have an engaging conversation without shouting over background noise.
Great Second Date Ideas:
A dinner table at a small, intimate restaurant
A sip of wine at a quiet wine bar
A walk in the park or along the beach
A fun but low-key activity like seeing art, making art, hiking, or farmer's market
Bad Idea:
A movie or concert (Might seem fun/easy, but no chance to talk!)
A party (Too many distractions! You need to focus on each other.)
A loud bar (Too much temptation to drink more than you should, and you can’t hear each other!)
The right person deserves your full attention, so choose an environment where you can truly connect.
2. Rushing Physical Intimacy Before You're Sure It's the Right Person
There’s often a question of whether or not to take things to the next level physically on a second date.
My advice? No.
It’s fine to try a smooch if you’re “not sure” but if you are sure and your body says no--please do not be tempted to any physical intimacy (including kissing) even if they offer, even if you are lonely, even if you’ve been drinking, even if you feel bad for them. It is the wrong message to send.
It's important to be honest with yourself and your date about your attraction. If you're not feeling it, don't force it. This is a good reason to also limit or avoid drinking altogether. Mistakes made while tipsy or drunk can add unnecessary years to your dating saga.
On the other hand, if you ARE feeling it, making out in public is fine, but that's it. Let the heat build, but do not rush anything because it distracts you from all the questions and experiences you need in order to really determine if the person is a match.
If there’s mutual attraction and you both feel the sexual tension, a kiss or flirty touches will feel natural. Good! But the key second date rules are about focusing on the conversation, and getting the answers you need to your 3H questions.
Good Sign: You’re both naturally drawn to each other, leaning in, making eye contact, touching each other, and feeling comfortable.
Red Flag: You feel pressured, unsure, or like you’re crossing your own boundaries to keep the other person interested or because you are enjoying their interest in you physically without having built an emotional connection.
If you’re unsure, ask yourself the right questions:
Do I see a potential future relationship here, or am I just caught in the moment?
Is alcohol or pressure affecting my decision-making? Do I feel uncomfortable or obligated?
Is this moving at a pace that feels right for both of us?
The best time to move forward physically is when a lot of trust has been built so that even if the sex is bad, you will be comfortable enough to talk about it and make it better.
3. Avoiding Honest Conversations – Get Clear on the Most Important Thing
By the second date, it’s time to start figuring out whether this person is truly a good match for you. That means asking good questions, observing their body language, and ensuring your values align. To do this, you are going to need to bring up harder topics, in regards to things that don't work about you or your life. A full explanation of how to talk about "liabilities" is here.
If you’re looking for a serious relationship, but they’re just interested in keeping things casual, that’s also something you need to clarify before date number 3—and before deep feelings get involved.
These are great questions that get at this on the second date:
“What are you looking for in a relationship right now?”
What have you learned from online dating?
What have you learned from past relationships?
“What are the important qualities in a partner for you?
“How do you usually approach dating?” What's been working/not working?
Having these conversations might feel nerve-wracking, but they can save you from wasting time on someone who isn’t the right match for you, and that is the best for you in the long run.
Good sign: They answer honestly and seem interested in your perspective. They ask similar questions back and show signs of active listening.
Red flag: They dodge the question, change the subject, or seem uncomfortable talking about relationships. This might mean they have unresolved issues or are not emotionally available.
The most important thing is to stay true to what you want—in terms of the seriousness of the relationship and the qualities in a partner you desire. If you aren't on the same page, abort the mission.
Setting Yourself Up for a Great Third Date
If you had a great time, felt a genuine connection, and saw potential for something long-term, then yay—you’ve set yourself up for a third date!
If things felt off, that’s okay, too. Not every second date leads to a next date, and that’s just part of the dating journey. The bottom line is that you want to be with someone who makes you feel excited about what’s ahead, not confused about where you (or they) stand.
At the end of the date, ask yourself if all 3Hs are happy:
Did I get evidence that our lives could work well together?
Did I feel comfortable and connected? Did the conversation flow? Am I intrigued?
Am I genuinely excited about seeing this person again? Did I feel chemistry?
If the answers are yes, then go ahead—make plans for a third date and see where this could lead! If not, it’s okay to walk away knowing you gave it a real chance.
Remember: Dating isn't actually about avoiding dating mistakes, it's about finding a romantic partner who aligns with the desires of your head (what's practical), heart (what you want to feel), and hoo-ha (your need for attraction). If you need more help defining the needs of each for yourself, watch my free webinar.
These tips to make your first 3 dates go smoothly are important, but the most important thing is that you get clear on exactly what you most desire and remove any obstacles to the fulfillment of that dream. I think the webinar will help.
There is an art and science to dating well and finding your person. It can be exhausting if you don’t know how to make the first 3 dates count, so make sure you read all 3 articles in the series!
Frequently Asked Questions About Second Dates
1. How do I know if my second date went well?
A great second date gives you a second chance to learn everything you need to know to fill out your 3H chart. If you got more answers, you should feel successful. If you feel comfortable, excited, and connected, it likely means you are both grooving with each other and are attracted. Did you get asked for a third date? That's the real sign it went well, but I think you can also call it a success if it was a bad date and you discovered dealbreakers and called it. The courage to keep an open mind is great, and so is the courage to say "no, thank you," walk away when you realize he's not "the one."
2. What if I’m unsure about a third date?
I ask my clients to rate their date in all 3 categories (head, heart, and hoo-ha) after each date on a scale of 1-10. All 3Hs need to be scoring above an 8 by the end of the 3rd date in order to proceed. Here's a reality check. "I don't know" or "I am unsure" is equivalent to 6.5. See, I just made something seemingly qualitative into something quantitative. That's really useful when it comes to being honest with yourself. If one or more of your Hs is at a 6.5, that's fine--it's not game over yet. You might not know enough to determine if they could go higher, but after the 2nd date, you only have one more date to find out if you're following my method. So you'd better get ready to talk about stickier topics!
Any red flags that are showing up by date 2 must be followed up on and either deemed solvable or "dealbreakers." Between date 2 and 3 is a good time to take stock of the attraction--is it growing or waning? If it's already waning, that's a bad sign.
3. Is it okay to bring up serious topics on a second date?
Yes! You must! If the person is attracted and wants to get to know you better, they will be happy to talk about all topics with you. If the chemistry is good, all of the topics become enjoyable. It's not a time to complain or trauma bond, but a time to talk about the things that are important to you, for example, what you've learned from past relationships, what you are looking for now (please go beyond cliches here), and what your deal breakers are.
4. Should I text after the second date, or wait for them to reach out?
Hopefully, you already told them on the date itself that you enjoyed yourself (if you did) and used a line like: If you asked me out again, I'd say yes. If so, it's in their hands to make that happen. If they don't reach out within the next 24 hours, that is NOT a good sign, but you can send a simple text checking in to confirm for certain whether or not there will be a future between you two. You'd write something like "Still feeling good about our time together, are you ready to plan another time together? If not, pretty please, just let me know."
5. What are some signs I shouldn’t go on a third date?
If any of your 3Hs aren't happy, as in the ratings on a scale of 1-10 went down vs staying the same or going up, that's an indication that the person is not your match. If you discovered any dealbreakers in the person, then the 2nd date should be your last date. Other red flags include inconsistent communication, excessive talk about exes, or feeling pressured into something you’re not comfortable with. A third date should feel like an exciting next step, not an obligation.
Love,
