Good Date Gone Bad | 7 Dating Mistakes Men Make

Posted by Todd in Relationships

dating mistakes men make Last night I was looking at our Christmas Day website traffic. Not only was it a lot higher than I anticipated (about 400 readers for the holiday), I was really surprised by what people were reading. The top articles were almost all about relationships. Our most read article during Christmas Day was 8 Reasons Why You Keep Getting Dumped. Isn’t that sad?? I recently was asked to begin writing a dating column for an alumni association I’m a part of, and Fearless Men is now featured on the Man Up Leadership App. With the requests we’ve been getting combined with what our readers were reading, I decided it’s time to write about Dating Mistakes Men Make.

Of course you can read the article on Getting Dumped, and John’s insight on How to Make Her Feel Special and First Date Tips will certainly get you rolling in the right direction. But have you ever headed out for a date confident it’s going to go great and things fall flat? Maybe you’ve been on several dates and somehow the oxygen gets sucked out of the budding attraction and things are suddenly dead on arrival? Learn what dating mistakes may be happening.

It’s not time to be frustrated with yourself or your dates. Let’s take stock and consider a few points that might be going wrong. Since the Getting Dumped article mentioned earlier is aimed at those that have been in a relationship for a while, I’m aiming this one at those men that have only been out on 1-5 dates.

Dating Mistake 1: You Don’t Have a Goal

I always aim to get to know one new, deep thing about a woman each time I’m out with her. I don’t put pressure on myself to know her life history or her plans for the future right away. I just aim to ask at least one good question, and take the rest of the date as pretty chill. Just go in without feeling the pressure to impress or know her life’s calling.

If it’s a first date, you MUST have a 2^nd goal, and that’s to nail down your next date. You don’t have to plan exactly what you’re doing, but set a day and time. Why? You want to keep the ball rolling while things are still warm. Don’t let her lose interest, and don’t let her walk away from the date thinking you didn’t enjoy the date enough to see her again.

If you don’t ask her out for the sequel by the end of Part I, the next time you try to communicate you should anticipate she’ll be in what some people call “auto-rejection” mode. You haven’t actually rejected her, but she may feel that way and be ruminating through those thoughts. Don’t be surprised therefore if she’s distant or slow to communicate with you about Part 2.

Dating Mistake 2: Playing the Waiting Game Like a Fool

Don’t let that horse get out of the gate too fast.

I don’t play waiting games. If I’m attracted to someone and we’re clicking, then I tell them I want to go out again. I’m not going to sit idly by like a passive boy waiting for her to chase me. If she likes me enough to go out with me again, then she’ll say yes. If she’s non-committal or distant, then I already know it’s not there and I don’t have time to pine away for her.

Listen, we’ve all got lots to do on this rock before we’re dead, so don’t make her wait 48 hours to tell her you want to go out again. If she puts you off after one or two dates, ask her out one more time and if she’s still cool toward you, move on man. There actually are other women out there. You were brave enough to ask this one out so just go do it again.

Now…if you’re already in a rhythm and have been on a few dates, you don’t have to feel the pressure to seal up the next date immediately. Once you guys have found a good pace, rushing to set the next time you’re going to be together probably isn’t necessary. Unless they ask. Then be polite and try to figure it out. Or at least tell them you def want to get back together and need to figure out what works.

There’s a lot of bullshit out there about waiting days after a date to call a girl. Don’t listen to that nonsense. Are you a player or are you interested? If you want to torpedo your chances with a fine lady feel free to take that advice.

Let’s get practical

“Oh God, I’ve never received a call on my phone before!”

If you want some practical advice, here’s mine. I could be totally wrong, but I think this is better wisdom than the average player advice out there:

Before your first date is over, tell her you’d like to see her again and decide when is a good time.
Don’t set up your next date any quicker than 4 days from now. Give yourselves a little breathing room.
- Why? It’s always easy down the road to speed up the pace than it is to slow it down. If you burst out of the gate running, in a couple weeks if you guys are hanging out every other night and you’re having second thoughts, it’s hard to slow that horsie down.
Text her within 4 hours of the date. Let her know you had a great time and are looking forward to seeing her again. Just don’t make her feel like you’re professing your love.
Call her within a couple days. Leave her a short and sweet voicemail that you just wanted to check in and say “Hey.”
- If she doesn’t pick up or call back it’s totally cool. If you’re dating someone less than 27 she might be allergic to phone calls anyway. But I still like to use them.

Dating Do: Be an Affirming Man

Find out something she’s excelling in and why she’s great at it. Then tell her why she’s so awesome. Make her feel attractive, but if you merely tell a woman she’s hot, not why—then you might be coming off as a sleeze. Try to find something uniquely attractive about her that you wouldn’t notice in other women. Point it out—it’ll mean a lot to her.

Again, compliments need to be original. They should be about how pretty she is, but they should also be about so much more. Find out why she’s incredible, and tell her what you’ve noticed. Slightly, casually, while giving her your focused attention.

If you can’t find something great and unique about her, you either don’t like her or you spend so much time talking and thinking about yourself you didn’t notice the gem she is.

Dating Mistake 3: Not Flirting

When I was 20 I was about to see a girl that I’d liked for a year but hadn’t seen in several months. I asked a mutual friend of ours, who is a woman, for some advice. She gave me one piece: don’t forget to flirt with her. I was confused, and asked her why she’d suggest that. She told me that sometimes guys forget to make a girl feel like he’s actually interested in her.

I think as men when we’re really attracted to and legitimately interested in a woman we sometimes become dead stiffs. Ever feel the cold sweat in your hands as you literally have nothing intelligent to say? Yeah, I feel ya. Make sure to bring your brain, and a little bit of heat. If you don’t show that you’re attracted and find her likeable, she probably won’t feel much of a spark. That’s a dating mistake men make.

Have you been out with a woman that was a total stiff toward you? You probably didn’t feel she was interested, and you’re attraction for her probably took a jolt too.

Dating Mistake 4: Being a Jerk Without Even Knowing It

Were you a jerk or were you nice? You might be quick to answer that you of course weren’t a jerk. But consider this: were you on time? Did you buy the meal/drink? Did you show up in a rush, sweaty, and kept looking at your phone the whole time?

If you didn’t show up ready, on time, and focused enough to give her your undivided attention, you might have come off as a jerk even if you didn’t say anything rude.

Dating Mistake 5: OCD

The flip-side of showing up with the tenacity to make her your entire world and make her feel like the center of the universe is this: you can totally freak her out. If you’re gazing through her face with the force of Superman’s Heat Vision and neglect to realize or refer to anything outside of her two-foot personal space, you might be coming off too strong.

“I only have eyes for you, baby.”

Dating Mistake 6: You’re hung-up on her and she knows it

If you’re hung-up on a girl within the first 3 dates, it’s going to be hard to not show it. You’re really attracted to a lady and love her company. You want it to work out so bad you feel the pressure to perform. Once this pressure builds, you’ll start to “grip” onto a relationship you never had.

Don’t let this level of desire for a woman build up-yet. If you are feeling that strong for a girl that quickly, you might be acting funny towards her. Inconsistent or extra emotionally sensitive. And that sucks the fun out of the fun stage of a relationship. Hey, as men we don’t like feeling pressured to be in love before we’re ready to be, right? Women don’t like to feel that way either.

If you’re dying to have this girl and are feeling a potential major letdown if you don’t win her–you’ve got to reduce the pressure on yourself man. You won’t act like yourself, and you won’t make her feel comfortable.

You’ve got to kill the tension while you’re on dates. Especially dates 3, 4, 5. Those dates are where a woman is wondering if a guy IS getting seriously interested in her or not. But if you go into those dates and you’re all wound up-it’ll be tense and you might kill off some of her interest. She may not know why, but she could possibly start feeling like the first 2 dates were great, “But I’m really not feeling it there between us anymore.” Don’t get sucked into that hole.

Here’s what I do to relieve the pressure on me: I know that not every woman will like me. In fact, most women don’t.

It’s really freeing to acknowledge this. Most women aren’t interested in me. Boom. If she changes her mind about me, no big deal. She’s not a bad person, and that doesn’t speak to whether or not I’m a good or bad guy.

If you can walk into a date carefree whether she accepts you or not, you won’t pander to try to endlessly impress her. Men who do that don’t come off as confident, rather they come off as people pleasers. And trust me, women aren’t drawn to that at all.

Dating Mistake 7: You don’t have any direction

So you’ve been out several times, now what? We don’t have space to cover that here, but at some point you’ve got to have a plan. If you’ve been out on 5 dates and you haven’t communicated with your lady friend whether your want to continue being casual, break it off, or really make an effort to get closer to her, your lack of direction may actually be allowing the “relationship” to die without your knowing it.

You don’t need to propose or tell her you love her. Just sit down with her and define together where you’re at, and where you’re going. Even if that means keeping the same pace and trajectory you’re at today.

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About the Author

Todd

He's a lover, not a fighter. But he's also a fighter, so don't get any ideas. He works for a series of private schools to advance innovative education to combat ballooning classroom sizes and challenge the status quo of the current public and private education format.