Biggest and Most Common First Date Mistakes To Avoid

Fact: first dates can be both exciting and nerve-wracking. You might be thinking, What should I wear? What’s the best way to make a good impression? And let’s not even start with the anxiety about awkward silences. But here’s the good news—most people make the same dating mistakes, and they’re totally avoidable!

Let’s dive into the biggest first-date mistakes you need to steer clear of and how to set yourself up for a great time.

1. The Dinner Date Trap – Why It’s the Wrong First Step

You might think a fancy dinner date sounds romantic, but in reality, it’s a big red flag when it comes to first date etiquette. Here’s why:

• Too much commitment. You’re stuck for a whole lot of time, energy, and expense with someone you barely know.

• Hard to escape. If the date is going south fast, you can’t just make a quick exit without climbing out the bathroom window.

• The wrong message. A lavish dinner can sometimes send the wrong message about how fast you want to go or how intimate you want to get. 

Better Alternative: Instead of committing to a full meal, start with a drink, coffee, or smoothie. That way, if you’re having a great time, you can extend the date into something more, like a walk through a favorite park or a meal.

Bottom line: The first date is your first chance to really check chemistry and rapport. If you're not having fun, you need to cut it short because "dating fatigue" is real. If you go on too many dud dates, you'll find yourself getting more and more cynical, and we can't have that!

2. Not Preparing for the Date – A Surefire Way to Have an Awful Date

The worst thing you can do is show up to a first date without a plan--about what you'll ask and say. A lack of preparation can lead to awkward silences, bad date experiences, and perhaps worst of all—sending the wrong message about your level of interest.

How to Set Yourself Up for Success

• Have some date questions ready. You don’t need a script, but a few open-ended questions will help you keep the conversation going. Avoid yes/no questions, and instead ask things like:

  • “What’s a cool thing you’ve done recently?”

  • “What’s your favorite restaurant and why?”

  • “If you could have dinner with any person (alive or dead), who would it be?”

• Pay attention to first date etiquette. Be polite, be engaged, and show up on time, and make eye contact.

• Know what YOU need to find out. Think about what you want in a long-term relationship and tailor your questions accordingly. Are you looking for someone with a great sense of humor? A decent human being who shares your values? Use your first date questions wisely!

Bottom line: Winging it isn't as cool as it sounds. Showing up unprepared is a dating mistake that could cost you a second date, but worse, it could cost you the chance to really get to know the person, which was the whole point to begin with.

3. Meeting in Private – Not Until After the Third Date

One of the biggest mistakes people make is meeting in a private place on the first date. Sure, being alone and private might sound appealing, especially if you're already attracted, but here’s why it’s a bad idea:

Safety first! A public place ensures that you’re in a safe environment and can leave easily if needed.

• First impressions matter. You want to observe your date’s body language, how they interact with others, and if they’re genuinely the kind of person they claim to be before considering the kind of fooling around that happens in private.

• Unnecessary pressure. A private setting can create an expectation for intimacy too soon, and that’s the wrong thing when you’re just getting to know someone.

Better Alternative: Meet in a public place like a coffee shop, a tea house, or a casual bar where you can chat comfortably and gauge your date’s vibe. If the conversation flows, you can decide whether to extend the date to a meal or a walk. Don't go anywhere private until you are ready to be monogamous (if you're into that) and you're open to having sex.

Bottom line: Always prioritize your safety and comfort. The right time for intimacy comes later—when you actually know and trust each other.

Want to Get A Second Date?

If you want to increase your chances of a second date, avoid these common first date mistakes and follow these bits of advice:

✅ Keep the conversation balanced. Let them talk, but make sure you also share about yourself! Don’t let the entire time be about them.

✅ Pay attention to red flags. If your date talks about past relationships the entire date, that’s a big red flag!

✅ Be present. If you’re distracted, checking your phone, or clearly thinking about the next morning, your date will notice.

✅ Assess compatibility. Do you share common ground? Would your life goals mesh well? Do they have a good sense of humor? Do they make you feel comfortable?

✅ Be yourself! You don’t need to put on a show or try to be someone you’re not. Don't send out a PR agent, show up as the real you. Trust me, it saves trouble in the long run. Confidence is attractive.

Want to know more about 2nd date mistakes, read here.

Best Way to Guarantee a Great First Date

The best way to make sure your first date goes well is to avoid these mistakes, come prepared to get your questions answered, and have fun. The worst that can happen is you get to meet a new human, who isn't the love of your life. Meeting new people, if you've vetted well is always a good use of your time.

At the end of the date, ask yourself:

• Did I have a good time? Was I laughing?

• Did we have a great conversation? Am I intrigued to learn more?

• Could I imagine kissing this person? Do I feel like this person has the potential for a long-term relationship?

If the answer is yes, then great—you just set yourself up for a better chance at love! If not, that’s okay too. There are a lot of people out there, and every date is a learning experience. Every time you admit someone is not the right match for you, you get closer to finding the last love of your life. Please be willing to tell the truth about it!

Your attitude about dating comes through in your vibes and you vibes are broadcasting out to everyone, and attracting what you think you deserve. If you need more help fixing your attitude or attracting a better caliber sort of person watch my "3 Secrets to Finding and Maintaining Love" Webinar.

Love,