How Women Can Avoid the Top Five Dating Mistakes
May 8, 2025
As a relationship expert, I have been studying dating over 50 for the last 20 years, and I have made an important discovery.
The good news is that the biggest mistakes women make in dating can be avoided.
First, let me introduce you to the 3H's. If you want a long-term relationship that is satisfying, you need to satisfy all three of your internal voters—your Head, Heart, and Hoo-Ha!
- YOUR HEAD: Your relationship should make practical sense. Your dating life should align with your real-life goals, and your dreams and your partner's dreams need to intertwine easily.
- YOUR HEART: It has to feel good. Your emotional needs—love, romance, honesty, humor—must be met.
- YOUR HOO-HA: Attraction matters! You have to want to kiss the person you’re dating.
If all three aren’t working (at the same time), it's not a match. Finding love isn’t based on luck—it’s based on making the right choices! Now I am going to lay out the findings of my research from the field regarding the Top 5 Biggest Mistakes Women Make in Dating...
MISTAKE #1: Saying Yes When You Mean No
I have to ask: how many times have you agreed to a first date just to “give it a chance” when your gut already said "no"? Or gone on a second date even though the red flags were obvious?
Stop settling! If a person doesn’t meet the needs of your Head, Heart, and Hoo-Ha, abort the mission! If he’s a nice, smart person, but there’s no spark, don’t force it. If he looks great on paper but talks about his past relationships the whole time, it’s a huge mistake to ignore it.
Best way to avoid this?
- If you feel indifferent or drained after a date, don’t go on another.
- Trust your instincts—if something feels off, believe it.
- Don’t let your female friends pressure you into “giving him a chance” when you know he’s not the right guy.
MISTAKE #2: Skipping the Video Call Before the First Date
You meet someone on a dating app—they seem amazing, so you jump straight into an in-person date night. But when you finally meet, you realize…ick.
Don't waste your time and energy. A quick video call before an in-person meet-up can save you from endless bad dates with people who just aren’t right.
Best ways to avoid this?
- Schedule a 10-minute video chat before the first meet-up.
- Observe their body language—do they seem engaged, confident, and real?
- If they dodge the call and insist on meeting ASAP, red flag! They are either hiding something or are not that interested.
MISTAKE #3: Texting Instead of Talking
Modern dating sites and swipe apps make it easy to fall into endless texting before actually spending time together. Real attraction happens in real life, not over text messages.
When you text too much, you:
- Create a fantasy version of someone who may not be a real person in real life.
- Waste time with someone who may not even be a good match.
- Avoid actual phone calls and video chats that would tell you much more about them.
Next time?
- Move to a real conversation ASAP—video call or phone call before a date.
- Pay attention to how they communicate—if they’re always on social media but take hours to respond to you, that’s a sign of where you rank in their life.
MISTAKE #4: Jumping into Bed Too Soon
This one is controversial, but let’s be clear—I’m not here to tell you when you should or shouldn’t have sex. But if you’re looking for a real, committed relationship, jumping into bed too soon can cloud your judgment.
A huge mistake women make is thinking that sex will lead to exclusivity or a deeper emotional connection. The truth? It won’t.
Best ways to handle this?
- Hold off on sex until your Head, Heart, and Hoo-Ha are all in agreement.
- Wait until you’ve had the talk about what you both want in a new relationship, monogamy and safer sex.
- Watch for red flags—is he pushing for intimacy before you’re comfortable? The biggest mistake women make is thinking they can change that kind of guy.
MISTAKE #5: Pretending to Be Someone You’re Not
Ladies, if you’re changing yourself to fit what you think a man wants, stop right now. If you pretend to love sports, downplay your ambitions, or suddenly become a different person just to fit into his world, you are not attracting the right men.
The right partner wants you for YOU. If you fake your way into a relationship, you’ll either:
- End up resentful that you can’t be yourself.
- Attract someone who loves a fake version of you.
- Waste months or years with the wrong guy when you could be with someone who IS a good match.
How to fix this?
- Be honest from the start—whether it’s about your family members, personal beliefs, or quirks.
- Stick to your own values—if you don’t want to date someone who parties too much or prioritizes career over relationships, stick to it.
- Don’t let fear of being single push you into a relationship with the wrong person.
Finding Love the Right Way
So many small mistakes can trip you up and make dating hard. But the best ways to attract the right match are simple:
- Be yourself. The right men will love you for who you are.
- No more settling for bad dates or ignoring red flags.
- Date with purpose. If you want a lasting relationship, don’t waste time on the wrong people.
- Get support. Work with a dating coach or talk to close friends to get an outside point of view.
Dating isn’t about finding just anyone. It’s about finding love that actually makes your life better. So, the next time you’re navigating the dating scene, remember—your Head, Heart, and Hoo-Ha all get a vote. And when they’re all in agreement? That’s when you know you’ve found the right partner.
Now, go date like you mean it!
Love,
Frequently Asked Questions About Avoiding Dating Mistakes
1: What if I still feel unsure after a first date? Should I give him a second chance just to be polite?
If you're unsure after a first date, don’t default to politeness. AIf your Head, Heart, and Hoo-Ha aren’t at least somewhat engaged (say a 6.5 out of 8 out of 10), that’s not someone you should continue seeing. “Giving him a chance” just because he’s nice is how you end up wasting months with someone who was never a fit. Women are conditioned to prioritize other people’s feelings—let’s break that habit, starting with your love life.
2: Why is a video chat before the first date so important? Isn’t that overkill?
Not at all! Think of it as a time-saving filter. In just 10 minutes, you can spot signs of anything off. Maybe something doesn't match what they said on their profile, or they aren't interested or together enough to make a video date happen. Don't you want to find that out before you waste time getting all ready and going out for a date? Also, you must check chemistry, that's good for both of you. If someone resists a quick video chat, they’re probably not being fully authentic. You’re not asking for a background check—just a conversation. It’s not overkill; it’s smart vetting.
3: How do I stop falling into “textationships” that go nowhere?
Texting gives the illusion of progress without any actual movement. If someone’s texting you all day but never asking you out or avoiding phone/video calls, they’re likely not serious about building a real relationship. Set a standard: if the texting doesn’t evolve into a real-world connection within 2 weeks, move on. A man who's serious about you will want to hear your voice, not just read your emojis.
4: Is it okay to have sex early if the chemistry is strong, or does that always lead to regret?
There’s no one-size-fits-all rule here, but here’s what I know: If your Head and Heart aren't as into him as your Hoo-Ha is, that chemistry can cloud your judgment. Having sex early isn’t inherently wrong—but if you’re looking for a committed relationship, it’s important to first confirm that you're both on the same page emotionally and that you're able to talk about sex and sexual health easily. A real connection can handle waiting. And if he bolts because you want to wait? Good. He just saved you time.
5: I keep trying to be “low-maintenance” so I’ll seem more dateable—what’s the harm in that?
The harm is that you’re training someone to love a version of you that doesn’t really exist. If you say you’re okay with something you’re not okay with—like last-minute plans or him never calling—you’re setting up a pattern that leads to resentment. Being honest about what you want doesn’t make you “high-maintenance”—it makes you emotionally mature. The right guy isn’t afraid of your standards; he’ll appreciate them and that you stated them clearly.