Are You Dating an Insecure Man? Here’s How to Handle It


I think it’s safe to say that there isn’t a person among us who doesn’t have dating insecurities. Some may be better at dealing with them or hiding them, but we’re all dating an insecure man to some extent.

Everyone has flaws and imperfections, and that’s perfectly normal. But, it’s the human condition to be painfully aware of them.

Our dating insecurities are part of who we are and don’t just vanish once we’re in a relationship. In fact, they may even become more obvious to you or your partner.  If you’re afraid you might get rejected because of the things you’re dating an insecure man about, then getting close to someone can make you feel very vulnerable. Will they still love me if they really get to know me?

But, what if your partner is the one who is struggling with hurtful, self-critical thoughts?

What to Do When Your Partner Is Insecure Man

It takes some level of maturity to become aware of these self-critical thoughts and be able to communicate them in a constructive way. If dealing with your own dating insecurities is difficult, facing your partner’s vulnerabilities can be even harder. Many of us aren’t fully equipped to address our partner’s insecurity, even if it is expressed in a constructive way.

Let’s take Erin and Ben’s relationship as an example.

Erin and Ben have been dating for months, and things were going very well until recently. Erin was very surprised when Ben started to need more reassurance about their relationship. He’d seemed so fun and had so many interests when they first started dating. But lately, he’d been asking her where she was going and who she was spending her time with. He didn’t want her to be with her friends and family unless he was with her. She felt that he didn’t seem to trust her. How to not be insecure when dating? Erin became frustrated with him and began to pull away whenever he approached her for more reassurance, leaving him feeling even more insecure man

Can you identify the weak point in their relationship?

They are not able to talk about a big problem they are having. Erin doesn’t communicate her frustration, so she pulls away, and Ben feels more insecure. Erin is missing an opportunity to stand up for herself in this situation. She could say to him, “Ben, I’m concerned that you don’t seem to trust me. I want to see my friends and family sometimes and I don’t understand why you aren’t comfortable with that. Can you please help me understand what is bothering you about it?

What You Communicate Is Always the Key

Your ability to handle a man who’s insecure depends on how well you can be clear with your boundaries. If your tendency is to try to please others rather than to be clear about what you need in a relationship, then you might tend to try and please or reassure an dating coaching for women over 40 and wonder why your approach isn’t working.

It’s important to also understand that it’s not your responsibility to “fix them.” Of course, you can be supportive, listen to them, and help in any way you can, but it’s not you who can fix this problem. It’s them.

It’s also very important to pay close attention to the dynamic between you and understand if some of the things that you are doing are making the situation worse, or if this is mostly his problem.

Erin might have been making the situation with Ben worse by pulling away from him rather than confronting him in a constructive way. By expressing her concerns, she was letting him know that she wanted him to address his insecurities in a different way. It’s then up to him to decide whether he can or will approach his problems differently.

You Must Set Boundaries

Dealing with an dating an insecure man doesn’t mean that you have to please them all the time to build their confidence up.

In fact, dating an insecure man gives you plenty of opportunities to be assertive. When you say “yes” or “no” to his insecurity, you are setting boundaries for your relationship. Saying “yes” is continuing to try and reassure him when it doesn’t solve the problem. Saying “no” is expressing your concerns as we discussed above.

Being Your Own Brand of Sexy is figuring out what you want, what works for you as an individual, and what strategies will help you to achieve your relationship goals, no matter what others’ opinions are about your dating checklist life.

Are you being your own Brand of Sexy? Take my FREE quiz to find out!

Over to You

Are you aware of your boundaries with a man? Is it possible for you to let him know when his issues are creating a problem for you?

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