10 Reasons Dating Today May Drive You Completely Crazy

It feels like dating will get you nowhere nowadays.

Last updated on Nov 27, 2023

Awkward date Africa images | Canva

Okay, before I tell you some of the reasons dating will drive you completely crazy, I also want you to remember something I live by. Being single isn't a bad thing. Being single gives you the opportunity to meet someone you've never met in your life. That little statement alone should excite you.

You might even run into the person you could spend the rest of your life with. The trouble is, that finding someone you really connect with can be like looking for a needle in a haystack. So let's talk about all the things that make dating a pain in the butt. Maybe it will help you negotiate the crazy, whacky world of dating!


RELATED: 5 Really Disappointing Realities Of Modern Dating

Here are 10 reasons dating today may drive you completely crazy:

1. Swapping numbers isn't a sign he's interested in you

That's right. Just because he took your number or gave you his, doesn't mean he wants to see you again. It doesn't even mean he wants to speak to you again. Why would he take your number if he wasn't interested? Most of the time it's because he's being polite, doesn't want to let you down on the spot, or because he lost interest during your initial conversation and took your number to get away.

2. First date weirdness

You swapped numbers, you actually set up a date, and now you're meeting. Now it gets interesting and, most of the time, very awkward. You want him to like you, he wants you to like him, you don't know anything about each other, you're not sure where he's taking you, you're freaking out you might have to eat in front of him and you're not even sure you're attracted to him.


Then you have to keep the conversation going, which can be a nightmare if you're with a shy guy or a man who is obviously totally terrified of you. Then there's the whole bill-splitting thing over dinner. I've said it a million times, going for dinner is a terrible idea on a first date. Avoid it like the plague!



3. Do you kiss?

You're going home after the first date. You like him, but you're not sure if he likes you. You've both read advice telling you how you should, "Play it cool," so neither of you is actually showing your true feelings.

It's like some weird game of relationship poker. Nobody knows what you're really thinking and that makes saying goodbye awkward. Do you kiss? Do you hug? Do you ask to see him again or leave it for him to make a move? If you kiss him, will he think it's a passport into your underwear? Will he feel rejected if you don't invite him in?


RELATED: The Surprising Dating Advice That Gets Real Results

4. The texting game

Now what do you do? Do you text him first? Do you wait for him to text you? Once again, both of you are playing it cool so you don’t know how he really feels. You’re worried you’ll come across as desperate if you text him, so you wait for him to contact you.

The trouble is he doesn't want to seem over eager so he's waiting for you to text him. The result is neither of you text each other so you both assume the date was a dud, and you move on, telling your friends, "I didn't really like him anyway. And his aftershave was horrible." All the while you're crying on the inside because you don't understand why another man "rejected you."

5. Intimacy scares you

You and the guy have finally told each other you're interested in taking things to the next level. You're going to see him again. Now you're wondering when you should be intimate with him. If you leave it too long he'll lose interest and cheat, and if you do it too soon he'll think you're easy and won’t want to commit, right?


Maybe you could go in for some heavy petting and see how that goes? But now you're worried you won’t be able to finish. Nobody has ever been able to bring you to that feeling like your first-ever boyfriend, but now he’s living in another state, he's divorced, and in a same-sex relationship with your old high school teacher! Yikes.

6. Your friends all become dating experts

When you're actively on the dating scene, all your friends suddenly want to give you dating advice about the men you meet. Suddenly all your friends know everything about dating, even though one hasn't had a boyfriend since she was 17, another one hates men, another is in a loveless marriage with a cheating husband, and the other one is jealous and bitter because you have nicer breasts than her.

RELATED: Masculinity Is Dead: Why Weak Little Boys Have Replaced Real Men

7. Being physical doesn't mean he's interested in you

When a woman sleeps with a man, it's a sign she likes him. When a woman is intimate with a man, it's a sign she wants to connect with him, and possibly start a relationship. When a man sleeps with a woman it often means nothing more than he wanted to blow his load and you're attractive to him.


Men do not equate intimacy with love and it's something women unfortunately have to get to understand. Just because he slept with you, doesn't mean he wants to date you. Sometimes, depending on the "man," it doesn't even mean he wants to see you again!

As a man, I wish it wasn't that way, but it's just the way it is. I don't make the rules here!

8. You now have to invest as much money as men

In the old days, men always paid the bill on a date, and call me old-fashioned, but I quite like it that way. But you ladies wanted equality, and in many ways, men have given it to you. One side effect of that is that a ton of guys now expect you to split any dating costs with them.

Now you have to invest just as much cash into dating as men do. It's time to start thinking about some fun dates that don't cost much!


9. You have to become vulnerable

That's right. If you're going to date, you have to accept you might have your feelings hurt (and let's face it, you probably will).

You're going to have to expose yourself. You're going to have to open your heart and risk men letting you down. It's just the way it is. Look at it as an experience. Think about dating as a journey of discovery. If a relationship doesn't work out, don't take it personally. Think about the lessons you learned, embrace the experience, and move on.

10. You could end up feeling silly

Yep, sometimes dating can make you feel silly. Picture the scene. You arrange a date. You get all dressed up, you head to the venue, you order drinks, and after an hour of standing alone, you realize you've been flaked on.


That's right. Dating is going to expose you to some flakes. They give you their phone number and then disappear into a cyber world never to be seen or heard from again. Sadly, you're going to meet a few "Caspers" in your lifetime so instead of driving yourself nuts, laugh about it.

You see, as much as dating can be a pain in the butt, it can also be a fun, exciting, passionate, magical, enlightening and life-changing experience. Stop worrying about when to call him, when to text him, when to be intimate with him, and start enjoying the experience.

It's time for us all to stop playing dating games and to become open, authentic, and vulnerable. I bet if we did that, we'd all enjoy love much more and probably have much better relationships!

RELATED: Why Modern Dating Has Made Me Stop Believing In Love


David Wygant is a dating coach who spent the past 20 years helping men and women transform their love lives. As a lead writer for Ask Men and Huffington Post, his advice has been offered across television, newspapers, and magazines, including MTV, The New York Times, MSNBC, Fox News, Cosmopolitan, Men's Health, E! Entertainment Television, and more.