What to Do When He's Just Not Interested In You

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Single ladies, I know dating can be rough.

It’s disillusioning to go on dates that lead nowhere or carry on endless talking phases before petering out. So when someone you really like comes along, you feel that it’s finally your chance. The apple of your eye could be a long-time friend, a first date, a voice on the phone, or nothing more than a picture on a screen. But you feel he’s a perfect fit! There’s only one problem. 

He’s not moving this relationship forward.

Maybe he is just shy, or doesn’t know you’re interested, or says he’s not interested in a relationship right now. So instead of giving up, you try to help it along. You might drop hints, offer your number, ask him out, or finally bare your heart. You ask him to reconsider or push him to change his mind. You tell yourself it really doesn’t matter how you end up together, as long as you get there in the end. Right? If you can just convince him to date you . . . 

Whether or not he actually does date you, you have two very big problems here.

You don’t want to date him as much as you think.

Women are uncannily good at talking themselves into feeling things (I should know; I’m a woman, too.) Odds are, you’re more excited about the idea of dating this guy than you are about the actual guy. When you’re crushing on someone, it’s easy to daydream about how great it will be to date, and you feel all the romantic feelings. When you try convincing him to pursue this relationship with you, you’re not actually chasing him. You’re chasing a relationship you’ve imagined, and you’re asking him to fill in the empty slot.

Convincing him into dating you sets the relationship up to fail.

Ask yourself, do you really want a man who doesn’t want you back? Or at the very least, one who doesn’t want you as much as you want him? Even if he likes you a little, he doesn’t like you enough to start a relationship with you. I’ve written before on this topic and the importance of moving on.

There’s a lot of insecurity for a woman in trying to force a man to be more interested in her. Even in the unlikely event this fellow sticks around long-term, you will definitely question whether he chose you because he loved you, or because you were convenient and pressured him into choosing you. Feeling this uncertainty is not a stable foundation for a relationship or marriage. You both need to feel desired, loved, and wanted in balanced measures. Don’t chase an imaginary relationship where this balance is totally out of whack, no matter how good his other qualities are.

Okay, you say, that all makes sense. But how do you apply this stuff to the actual dating world? How do you know if you’re convincing someone to date you? Or are you just in the thick of the normal dating maze? The two can be confusing. Here are some helpful questions to help you sort it out:

Are you confusing being intentional with being desperate?

Being intentional is being honest with your dates about what you want, what you value, and why. Being desperate can incorporate all those things, too. The easiest way to spot the difference is when you share all these things. Desperation often leads you to “heart-dump” your expectations and baggage way too soon and at a stage in the relationship when trust has not been established. If you find yourself pouring out your heart to new dates or strangers on the phone, you’re probably coming across as desperate, not intentional. Time to practice healthy boundaries.

Are you being too vulnerable with someone who hasn’t earned it?

Early on in the dating game, it’s crucial to be honest about yourself and your expectations. But this doesn’t mean being vulnerable right off the bat. The first text, phone call, or even the first date is not enough time to establish trust. Just because you feel like you can tell him everything, doesn’t mean you should. Doing so can make you think this man understands you and your happiness depends on him . . . when in reality, you blindly handed your heart to a stranger who never asked for it. Instead, bide your time. Stop acting on infatuation. Wait for him to prove he is worthy before handing him your trust. Don’t treat him like a romantic partner if he’s not your romantic partner! 

Are you addicted to winning him over?

Convincing uninterested men to date you can actually be a form of addiction. Maybe you have a pattern of getting really excited about a new guy and doing everything you can to get his attention. But then, if/when you finally get him to go out with you, everything falls flat. You were so sure this was the right one, but you feel bored and deflated when you’ve finally got him. Take a step back and see how many times this has happened. Are you pursuing good relationships, or are you chasing the high of “winning” a cat-and-mouse game? You might be hooked on the emotional high of infatuation, combined with the ego boost of winning someone’s attention. This obviously will hold you back in your pursuit of a good relationship. Time to reevaluate your approach to dating.

Do you think he’s the ONLY one for you?

“One-itis” is the common trap where a single person gets hung up on someone else who isn’t interested in return. There’s a tendency to put this uninterested crush on a pedestal. Then the woeful single assumes no one else in the whole wide world could measure up to what this person could be . . . if only they would just date you.

Obviously, this will kill your dating prospects, because it kills your interest in other people. And that will, in return, kill their interest in you. So, accept there’s no one single person who you’re predestined to marry. There’s plenty of fish in the sea, as the saying goes! There are many, many good men in the world. And a lot of them will be interested in you! The best way to move on is to go out and talk to new people instead. You never know where it will lead.

It’s pretty clear that if you find yourself having to convince, cajole, or talk a guy into dating you, this is not the relationship for you. You should step back and let go of the imaginary future with him. You deserve so much more out of a relationship than a reluctant boyfriend! Focus on meeting other men who are actually interested in dating you. Trust me, there’s plenty–and CatholicMatch is a great place to find them!

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