6 Mistakes I’ve Made in Dating

6 Mistakes I've Made in Dating | Millennials with Meaning

Dating is a pretty big deal to me. I don’t date just to date and I don’t date just anyone. My dating history isn’t incredibly lengthy, but it’s enough of a history for me to have learned a few things. (It takes all of one date for that, am I right? 😊) Here are six mistakes I’ve made in dating:

  1. Reaching out when I haven’t heard from a guy. When the phone goes silent, it can be tempting to say something seemingly “harmless” to test the waters, and I’ve done this two too many times. (Well, technically my friend did it for me once.) REALLY DUMB ROOKIE MISTAKE. This one’s for the ladies: If you have just started seeing a guy and he’s not responding, resist the urge to reach out. Or, in my case, don’t let others talk you into it! If a guy’s interested, you’ll hear from him eventually (usually within about four days, but there are exceptions). The last thing you want to do is look desperate. You can reciprocate, but don’t initiate. Let him be a man and pursue you, or he won’t think you’re worth pursuing. And you ARE worth pursuing.
  2. Dressing too casually. There’s absolutely no problem with being yourself and dressing in a relaxed style – especially because you want to feel relaxed on a date and take the pressure off both of you! But when I look back on things I’ve worn on a date, I could have dressed up a little more to show that I put extra effort into my appearance. You don’t have to wear a dress or a suit, but do make it obvious that you tried. It makes the other person feel special.
  3. Being too sarcastic and negative, even jokingly. When I was young and stupid and wanted to impress someone, I took every opportunity I could to make myself look smart, since I thought that was my best attribute. I may very well have come across as intelligent, but I’m pretty sure I also came across as a jerk, a know-it-all, and a downright disrespectful date. Joking around is totally fine. Just don’t do it at the other person’s expense. You don’t know them well enough yet! Doing this in the past remains one of my biggest regrets. Never talk down your date, even as a joke! If you must make a snide remark, at least do it at your own expense.
  4. Ordering food that’s messy or hard to eat. Before my first date, I read dozens of articles on what to wear, say, and eat. Most of them advised to just relax and be yourself, so I did! Tried to, at least. I ended up messily slurping an ice cream cone, fighting to keep it from spilling as it melted in my hand. And then kicking myself for not thinking about this scenario ahead of time.
  5. Letting my friends convince me to do what my gut tells me I shouldn’t. This often goes back to #1 for me. Every single time I’ve waited to hear from a guy I’m dating, the vast majority of my friends have urged me to text or call him first. Except my male friends – they emphatically say not to (In every experience I’ve had, they’ve proven to be correct). I’ve also had friends encourage me to wear outfits that just aren’t me, try to talk me into dating guys I know are wrong for me, and insist I invite a guy I’ve only just started seeing to a formal event. I’ve listened to some of these suggestions and ignored the advice of others. But the moral of the story is that when you have a gut feeling, follow it! It doesn’t matter if other people do things differently in their own relationships. Do what YOU think is right in yours!
  6. Meeting my date somewhere instead of having him pick me up. To be fair, there can sometimes be safety concerns with this, so I get why some people don’t want to disclose their addresses at first. But I would also pose this question: if you aren’t sure this person can be trusted with your address, should you really be dating him? (I’m preaching to myself here.) If you think this is a safe enough person to date and you’re a woman, let him be a man and pick you up for your date. If you’re a man, BE the person responsible for her safety and drive her to and from your destination.

Whelp, there you have it! My list of future dating don’ts. Although I’m certain I’ve made countless other mistakes in dating, these are the ones that tend to haunt me. Live and learn, right? 🤷🏼‍♀️

Now you tell me: what are the biggest dating mistakes you’ve made? What would you do differently in the future?

6 Mistakes I’ve Made in Dating

Braking Up is Hard to Do

6 Mistakes I’ve Made in Dating

7 Things to Consider When Choosing a College

Newer post

There are 2 comments

  1. K8

    I think dating before really knowing the guy was my first mistake. Another one was not recognizing when he was not interested in what was going on in my life, which was a sign we were probably over awhile before that.

    1. millennialswithmeaning

      I agree that it’s a good idea to know some basic information about the people we go out with, although the one good thing about not knowing someone well is that there’s no shortage of things to talk about! And I think sometimes we’re so optimistic in the early stages of dating that we miss signs that might be obvious to others. That’s where I rely on others to help me see what I’m missing!

Post a comment