By · @the_popular_man  ·  · 65 Shares

A friend told me about her experiences on several dating apps. She was bragging about all the dates she’d gone on and how “successful” she was at dating. What she meant was that she had a lot of Tinder matches, got a lot of attention, and went on some first and second dates.

After a couple of dates, her success was less than stellar. She was great at matching, decent at getting dates, but not very great at getting into a relationship. Although she could take comfort in the fact she was attractive and guys liked her, it was a consolation prize for her main goal: a loving, long term relationship.

If you are the type who can get attention and go on dates, but can never get into a relationship, here are a few things that might be getting in your way.

Before people object that they just need to be themselves, let me add I’m all in favor of that. However, sometimes being yourself, especially if that means continuing to do unattractive behaviors, means being single too.

Instead, I advise being your best self through self-improvement. You keep your core values, but work to be the most excellent version of yourself. With that in mind, here are some reasons why you can’t get into a relationship.

You’re Boring

4 Reasons You Can't Seem to Get Into a RelationshipA good friend of mine liked a girl who was very physically attractive. He went out with her a few times, but then suddenly stopped dating her. I expressed my surprise that he would give up such a good looking woman. He replied that she was just so boring that he didn’t enjoy spending time with her.

You might be physically attractive, but if you’re no fun to talk with, you only like to sit around, or you show no enthusiasm for life, your physical traits aren’t going to overcome your sheer lack of personality.

The good news is that very few people are boring from birth. While some are more extroverted or introverted, the ability to be interesting and have fun (or not) is usually learned.

Parents, teachers, religious leaders and others like to tell us how we should or shouldn’t act, so we might hold back from expressing our natural personal energy. Sometimes people get so used to getting by on their looks, they stop working on their personality. Whatever the reason you are boring, change it!

Read up about interesting things, have new experiences, open your mind to fun and exciting activities, and leave your comfort zone. Not only that, but then express your newfound interests to others. You’ll not only come across as exciting, but your life will be more fun because of it.


  • Got fired from McDonald’s when you were 16?
  • Been dumped 6 times and don’t trust men?
  • Hate the job you’ve been doing for 20 years?
  • Your dog ran away when you were 7?

If you had a rough life and complain about it often, you might be justified. But, to everyone else, you’ll just come across as angry and bitter.

I have empathy for those with problems and so do many people. But, there are two reasons you don’t want to complain and appear bitter when dating.

First, when you start dating someone, you want to put your best foot forward. Most people don’t find bitterness attractive and don’t consider complaining a good date conversation topic.

Second, being a problem solver is considered an attractive trait. Being a victim, on the other hand, isn’t. If you’ve overcome adversity in life, that’s a good thing. You can talk about the overcoming, not how the adversity made you angry or continues to do so.

Bitterness comes from a lifetime of hurt, so it’s hard to get over quickly. But, my best advice is to focus on the positives in your life and your role in creating those positives. And, at the very least, focus on that during dates. Everyone understands their date has issues. They just don’t want to hear about them all the time.

You’re Stuck On An Ex

I dated a woman for about a month who always talked about one of her exes. She mentioned how much she hated him, how bad he was for her, how glad she was to be rid of him, and how he was a deadbeat dad for her daughter. She might have thought her comments would show me she was over him. Instead, she told me the opposite.

She clearly had a thing for her ex-boyfriend. It might not have been love, but it certainly was hate. Whatever it was, he occupied more space in her head than I could ever occupy. If you constantly think and talk about another person, here’s a newsflash: you’re not over that person. And, I believe all of those obsessions are ultimately rooted in love, even if it’s “I love him so much that I hate him.”

Plus, one of the last things your dates want to hear about is your past relationships. It ranks up there with your bathroom habits and that zit you had in 7th grade. It’s because no one wants to be second place in a relationship. And, when you talk a lot about an ex (even to badmouth him or her), it tells the person you’re currently dating that you still have a thing for a past partner.

Even if you’re not fully over an ex, at least keep quiet about it during a date. Everyone has leftover attachment and issues surrounding an ex. The key is to work through it, whether with friends, a therapist, or your mother. But, don’t discuss it on dates.

You’re Flaky

I didn’t have to hear the woman in the previous section talk about her ex all the time. It’s because we rarely had a full date because she was late every single time. That, of course, doesn’t include when she changed the place I was meeting her several times or, one time, decided not to show up at all. Needless to say, I cut it off after a few weeks.

If you’re not getting into a relationship, it could also be because you’re flaky. Most people are patient and understanding. If you get in a traffic jam or your uncle is in the hospital the average person won’t hold that against you. But, if day in and day out, you’re canceling dates or constantly arriving late, then people will get sick of it.

When you date someone, that person wants to be your priority, or at least a priority. When you’re constantly late or flaking for one reason or another, you’re showing the person you’re dating that he or she isn’t enough of a priority for you to be on time.

On a basic level, stick to your commitments. If you say you’re going to be at a place at a certain time, then make an effort to do it. Don’t make plans if you have no intention of keeping them. In a way, these behaviors are about being an adult. But, if you haven’t learned that, then now is a great time to grow up.

So, if you’re constantly getting dates, but not into a relationship, these four behaviors could be playing a role. Work on them and others will be more likely to want to be around you long term. Be yourself for sure. But, above all, be your best self.

Is there a special guy you have set your sights on, but you don’t know how to get him? Do you wish you knew what to do to make him yours? Claire Casey’s Capture His Heart is exactly what you need. For a step-by-step guide to wrapping that man around your finger… CLICK HERE!

Jonathan Bennett

Jonathan is an author, relationship expert, and counselor. He owns a consulting business that helps men gain confidence and attract the woman of their dreams.

Author, consultant, and relationship expert, he runs The Popular Man and Love Advantage

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