There’s a painful downside to dating that you won’t see mentioned on many blogs, but it probably makes up half of many guys’ dating lives.

I’m talking about being single for so long that it almost feels like you’ll date anyone who comes along and is into you. The longer you go without finding a woman who meets what you’re looking for, things keep getting quietly stricken from the list of qualities you insist on finding in a woman.

It’s frustrating sometimes to see lots of friends (or even strangers) around you coupled off into great relationships while you stay single for much longer than you’d like.

Maybe you even start feeling like you’re missing out on “dating experience” in this period. You need to spend time in relationships to learn how to be in a relationship, right?

In this state you may be more susceptible to letting red flags slide, as long as you get to date a woman who reciprocates your desire to be seeing someone romantically. This erosion of standards can lead to some painful months or even years, while you spend your time with someone you don’t actually get along with.

When you’re starting one of these, you feel hopeful and excited because you’ve regularly started seeing someone new!

But finding the best relationships depends on doing your best to make sure that your efforts are not going to waste as well as looking out for yourself and your needs.

It requires some mental gymnastics (and a bit of denial) to do otherwise. Let’s talk about this.


CAUTION: Spend your precious time only on the right women

People do learn lessons and learn about themselves by being in less-than-ideal relationships, and even learn from being hurt emotionally. But that is no reason to stay in one you KNOW is bad — once you notice that, you should do something about it and quickly.

This exact thing I’ve been describing has happened to me. One summer, I had started dating a woman who had some very attractive qualities. She was energetic, extremely smart, and gorgeous to boot.

But I ignored the warning signs.

I should have seen right away that we were NOT right for each other, but it was thrilling to have some attraction reciprocated. Maybe I was feeling lonely and just a tiny bit desperate.

So we dated for three months, seeing each other once or twice a week. Three months!

To be frank, she turned out to have a lot of qualities I just don’t enjoy in a person. She showed unchecked selfishness and some heavy insecurities, and wasn’t reliable when it was important to me. Most of these kind of stayed hidden until we had time alone.

However, she was easy to introduce to other people, fun to be around while out on the town, and did I mention gorgeous? It was confusing and I admit I was a bit of a pushover at the time.

I enjoyed compliments from my friends on her looks, and at the time it made me happy to notice that they were a little envious of me.

Things came to a halt when she failed to respect my boundaries in the bedroom two different times. Suddenly all of the things I had been ignoring came into focus.

I’m glad I made the decision to end it while we weren’t too deeply attached, and I’m sure you have felt the same way if you’ve had a dating experience like this.


Listening to how you REALLY feel, not how you think you should feel

Looking back it feels like such a waste of time, but I realized that at least I learned this lesson from it: always reflect on what is working and what is not, and if important aspects of the relationship are broken it’s probably best to let this one go.

But how do you know when it’s time to call it off? It could be an obvious event, like what I described above, of course. But what if it’s more subtle?

On the one hand, it can take a bit of time to give yourselves a chance to grow on each other and learn things about one another’s personalities. You can’t always expect an immediate “spark” or deep infatuation. Actually, quickly falling in love like that can be a bit of a trap!

It can be kind of nice if a woman you’re dating is not an open book from the start. It gives you time to develop feelings and comfort with her, right?

On the other hand, you need to be wary of things that will hurt the relationship down the road, or worse — hurt you. It’s not a red flag to think “I’m not feeling head-over-heels for her right away!” But intense jealousy or psychologically abusive behavior are definite things to stay far away from.

So how long is too long? Only you can really know the answer to that. But maybe a good friend or two can help by listening to how you feel about it.

A second pair of ears might be all you need to get clear on what you want to do.

It comes down to whether or not you feel like there is a budding sense of connection, good fit, and fulfillment. The element of sexual attraction can be very important as well.


You deserve to be in the best relationships. Don’t ever sell yourself short because of a dry spell, frustrations about not “finding the one,” or the opinions of your friends.

Good friends will try to help you get to where you want to be if you need it, and will be there for you if you need to talk it out.

And imagine the confidence you’ll feel knowing that you have the power and ability to take control of your dating life the way YOU want to.

I believe you can do it. The right woman and the right time will come, probably sooner than you think.