Most Common Third Date Mistakes to Avoid
May 1, 2025
Now is a good time to read about the mistakes of date number 1 and date number 2 to set the stage for this article about the importance of the third date.
The 3rd date is a milestone, it assumes you are really interested in each other and attracted– but there are still some very important things to get clear on before you can proceed further.
WARNING: Once you have 4 or more dates with a person, you unconsciously become “invested” even if the person is not a match..
That’s why Date 3 is pivotal and the one that should be your inflection point, where you decide whether or not you meet each other’s (FULL) criteria for a deeper connection.
If you are following my 3H method, you know the third date is a pivotal point. I'll assume you’ve had a great time on the first date and second date, but now you’re faced with a crucial question—are you on the right path toward something long-term, or are you about to fall into some of your old bad patterns and end up unhappy in the long run?
By now, you’ve probably tested out your body language chemistry, enjoyed each other's sense of humor, and established some sexual energy. But before you get swept away, let me teach you the third date rule and the deal breakers to look out for to save you time, energy, and emotional stress.
And now, the most common dating mistakes people make on the third date:
1. Avoiding Dealbreaker Conversations in Early Days
By the third date, you must move beyond surface-level chatter. This is the time to discuss the important questions about your "must-haves" for a long-term relationship.
I mean questions about addictions and bad habits, general health conditions, what family life looks like or could look like, where you see yourself in five years, and so on.
One of the most common mistakes people make is avoiding these conversations because they don’t want to “ruin the mood.” But—it’s better to ask now than to waste months (or years) realizing your visions for life and your values don't line up.
Key Third Date Questions to Ask Potential Partners:
- “What are you looking for in a relationship?”
- "What have you learned from past relationships?"
- “How do you view commitment and monogamy?” What's your definition?
- What have past partners said are your bad habits?
- What concerns do you have about your health?
- "What are some dreams you want to fulfill in the next 5 years?"
- “What role do family members play in your life?”
- “What are your thoughts on how finances in a couple, and what are your future goals in this area?”
Some of you will be afraid to bring up what seem like awkward topics. Quick tip: Share about something in your own life first and then ask what your date's experience has been with the same issue.
For example: "In one of my past relationships, I discovered my partner and I had very different concepts of monogamy, and it led to a lot of pain. What has been your experience?"
Or, "In one of my past relationships, I found myself becoming the sole financial provider, and it slowly made me so resentful and eroded the love. I told myself I wouldn't let that happen again. What has been your experience with money differences in relationships?
2. Rushing Physical Intimacy in a New Relationship Before Establishing Monogamy
Here's a very common question—should you sleep with someone on the third date?
Maybe you thought the third date rule was that by Date 3, you should be ready to take things to a deeper level physically. Nope, it's not likely to be best when it comes to finding "the last love of your life." I know I warned you off in the date 2 article, and now I am warning you off yet again!
It can be tempting to have sex earlier than is best for you emotionally and psychologically. Sometimes, people do it thinking it will win the other person over, and some people try it to “see” if they’re attracted or could become attracted. Some people just want to have sex. No judgment, but if you’re looking for your forever person, I suggest waiting until after Date 3 and agreeing to monogamy before having sex. Read more about the 4 Steps to Establishing Monogamy here.
A common mistake people make is believing that sex will deepen their connection, when in reality, it can sometimes create problems. Emotional attachment can cloud judgment, making it harder to see potential red flags and incompatibilities.
Why Waiting For "The First Time" Is the Best Move:
- It ensures you’re both aligned on relationship expectations.
- It helps prevent false emotional bonding that might not be based on real compatibility.
- It allows you to continue exploring each other’s values and goals before making a big emotional investment.
If you feel comfortable moving forward physically, great! Just make sure it’s because you want to, not because you feel pressured by an unspoken dating game rule. The right person will respect your boundaries and be willing to wait. And the waiting should only help the heat to grow and ensure that it will be a fun, connected experience once it does happen.
3. Staying in a Situationship Without a Good Reason
Here’s something a lot of people don’t want to admit: They keep dating someone even when they know it’s not right. Maybe they like the attention. Maybe they don’t want to be alone. Maybe they think the person will change over time.
Your last ethical chance to tell someone it’s not a match, before you’ve wasted too much of their time or had sex and gotten attached, is date 3. It’s just not nice to continue on--avoiding being lonely, at the cost of you both finding your forever match. It just decompensates later and becomes way more heart-wrenching.
Signs You Should Walk Away:
- You feel more obligated than genuinely interested.
- You catch yourself ignoring red flags because you’re enjoying the moment.
- You’re forcing attraction that isn’t naturally there.
- You wouldn’t introduce them to your best friend
If you wouldn’t be thrilled to introduce them to your family members or invite them to an important event, why are you still seeing them?
The Real Third Date Rule
The real third date rule has nothing to do with sex or game playing--it's a way to force yourself to poop or get off the pot.
Only allow yourself 3 dates to determine if someone is the right match for you--head, heart, and hoo-ha.
Preparing for the Next Steps
If you’ve made it through the third date and still feel that spark, excitement, and compatibility, congratulations! You’re building a real connection with potential for a healthy relationship.
If you’re unsure, that’s okay too. The third date is a pivotal point—a chance for a full body yes or a firm and freeing "no."
At the end of the date, ask yourself:
- Did I get my questions answered, and feel our values and dreams are aligned?
- Do I feel sure there are no dealbreakers present?
- Did we discuss liabilities and manage not to scare each other off?
- Are we building a connection on a deeper level?
- Do I feel excited to do a bunch more things with this person?
- Could I imagine looking at this face forever?
- Is there a real chance for this to become a long-term relationship?
If the answer is "yes" to all of these, then go ahead and plan that fourth date (and start to plan when you're going to have the "monogamy before sex" talk!) If not, walk away with confidence knowing you gave it a fair chance.
What you want is to find the right person—not just keep yourself entertained. The best way to build a solid foundation is to be ruthlessly honest and curious at the get-go. Set clear intentions and bring your date on your ride--if they are your person, they'll appreciate your honesty, clarity, and efficiency.
For more on how to choose the right person and get out fast if it's not right, watch my free webinar.
Frequently Asked Questions About The Elusive Third Date
1. What should I expect on a third date?
The third date is when things start getting real. By now, you’ve established chemistry, shared some laughs, and started forming an emotional connection. This is the point where deeper conversations about values, relationship expectations, and long-term compatibility should be completed. It’s also a great time to discuss your views on monogamy and even establish monogamy if you intend to start having sex.
2. Is it too soon to discuss relationship expectations on a third date?
Not at all! In fact, avoiding this conversation is one of the most common dating mistakes. You don’t need to plan your future together just yet, but asking questions like “What are you looking for in a relationship?” or “What's your definition of long-term commitment? Of monogamy?” can help determine if you’re on the same page.
3. How do I know if we’re moving too fast physically?
If you feel pressured or unsure about taking things to a more intimate level, that’s a red flag. The third date does not have to mean sex. The best approach is to check in with yourself—Am I doing this because I genuinely want to, or because I feel like I should? If you’re not comfortable yet, communicate your boundaries. The right person will respect your pace. Being honest is really the only way to weed out people who aren't right for you. It's a must!
4. What if I’m still unsure about them after three dates?
Uncertainty is normal, but if you’re still feeling “meh” about them after three dates, it's a sign they’re either not the right person for you or you simply have not been saying what you desire and asking all your questions.. If you haven't asked and said everything on your mind, there is no way to be clear about the potential for a long-term relationship. If you have and you're still feeling indifferent (a 6.5 on a scale of 1-10), then abort the mission! Time's a-wasting.
5. When should I stop seeing someone after a third date?
My goal for my clients is that your head, heart, and hoo-ha are all giving thumbs up signs after the 3rd date. That means you'd rate the person 8 or higher on a scale of 1-10 in each of the three categories--meaning they are a smart choice, they feel good to you, and you are attracted. And that's not all. You have to want to introduce them to your best friend or family members. That's how you know you are impressed. They also have to be looking for the same thing you are--casual or long-term, and they need to indicate that you are rating high in terms of their criteria.
If any of the H's isn't 8 or above, no fourth date! This requires you to ask great questions on your date and for you to be honest with them and yourself about what you really want. Simple, but not easy. This is why I designed an entire course to support women over 50 in the pursuit of love. Access it here.
Love,