Dating Lessons I Wish I Would Have Known Long Before I Started Playing The Field

April 22, 2015  |  
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As a woman slightly over the age of 30, I have a few years of dating experience under my belt. I’ve dated all kinds of men, from the least to the most desirable. I’ve had good dates and others I wish I could forget. I’ve been a good date and, shamefully, been a bad one. Committed relationships have blossomed from some situations and friendship from others. Some dates even ended up being an enemy. Despite my wide array of experiences, there are some things I wish I’d known before I started dating in my teens. And while the experiences I had at age 17 are different from the ones I had in my 20s, as they should be, there are still some things that transcend age.  Here are a few dating lessons I wish I would have known about a long time ago.


Dating should be fun

When I was in my teens it was fun. Then the older I got the more serious I became about dating. I only wanted to go out with guys I could see myself being with long-term, and I took a lot of things way too serious. Some dates should have just been mini adventures to meet new people and have a good time. Have more fun with it!

Every man you date is not your potential husband

To piggyback off of the aforementioned suggestion that dating should be fun, remember that every man you date is not meant to be your potential husband. It’s just a date. Relax. Who knows what can come of it? He could just be a great guy who teaches you more about what you do or do not want in a future mate. I’ve learned great lessons from men who I hung out with only once or twice.


It doesn’t hurt to date men who are not your type

So he’s not as tall as you’d like, he could use some help with his fashion sense, and, to be honest, you’re not in love with the way he looks. So what? If you enjoy his conversation, it’s okay to go out on a date with him. You may be able to get past some of the superficial traits that he doesn’t have. It’s okay to date men who don’t meet all the qualifications on your checklist.

It’s okay to initiate a date

Although I am a borderline feminist, I am somewhat old-school when it comes to asking a man out. In most cases, he should do it. However, if he’s showing interest and moving too slow, it is okay to initiate things. What does this mean? You can simply say, “We should hang out sometime.” It’s a more subtle way of initiating a date. If he’s interested, he will follow through with plans.

Don’t always rule him out after the first date

You never get a second chance to make a first impression. I agree with this for the most part. But in the bleak dating world, if you weren’t impressed with him on the first date, it’s okay to give him another shot if he asks. Maybe it was first date jitters, or maybe he was having a bad day. Whatever the case, don’t be afraid to try again instead of ruling him out immediately after the first outing.

It’s okay to “date” multiple guys

If you are not in a committed relationship, it is okay to date multiple guys. If you and your main guy have discussed being exclusive, then that’s one thing. But if you are dating a guy who is showing no signs of wanting to commit just yet, or if it is too early on in the dating process, it is okay to go on dates with other guys. You may miss out if you put all your eggs in one basket.

Ask the right questions on the first few dates

If you do decide that you’re feeling the guy you are on a date with, or you at least want to rule out the phonies, make sure you ask the right questions in the beginning. Is he dating someone? This is important because you don’t want to be in a crazy or dangerous situation with the girlfriend he conveniently forgot to mention. Does he have kids? If you are dead set against dating men with kids, it may be best to ask this in the beginning. Also, find out what he does. It’s not for the sake of trying to count his money but to ensure that you won’t be guilty by association in some illegal activity.


Pay attention to red flags

He continuously has to cut dates short. He won’t go to certain places with you. And he has an excuse for it all. Pay attention to red flags at the beginning of the dating process so you won’t end up in a committed relationship with the wrong dude. So many times I ignored red flags because I liked the guy. This was early on in my dating life. As I matured, I became the queen of spotting shadiness quickly. Make sure you’re on the lookout early on.

A man is not always the person that shows up for the first date

I’ve met some great guys on first dates, but I’m not sure who showed up on the dates from that point forward. Now I know and have known for quite some time that most guys are goody two shoes on the first date. The true test is how they act after you really get to know them.

Take it slow

Do what you want in your dating life, but I’ve learned that taking it slow whether with sex or jumping into a relationship, is usually the best option. There are some really good stories that come from people who have experienced finding love at first sight. I am not one of them, so I choose to take it slow and really get to know the person I’m dealing with.


It’s okay to cut a date short

Just because you accepted the date doesn’t mean you have to stay on it if it is going horribly. Why torture yourself or the other person? I’ve had some bad dates that should have ended after 10 minutes, but instead, I sat through dinner and felt obliged to continue for the trip to the movies. Why make a bad date any longer than it has to be, wasting both of our time?



Be honest

Being honest sounds pretty self-explanatory, but if you are not looking for anything serious and the person you’re dating is, be open and honest in the beginning. If you are seeing multiple people and your date is looking for exclusivity, make things clear immediately. I failed to do this more than once and hurt people in the process. And although it was never my intention, those hurt feelings could have been prevented if I would have communicated clearly and honestly off the bat.


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