Insecure in Your New Relationship?

Posted by in dating after divorce, love after 40, self-esteem in dating, single women over 40 | 2 comments

Dear Sandy,

I am new to dating so it is still quite awkward.  I have been dating a great guy for about a month now, but I find myself expecting more than I should be.  I don’t know how to keep myself from feeling this way.  I am keeping these feelings hidden from him as best as I can, but when we are apart I am a mess and paranoid wondering why it isn’t going further, what is wrong with me… Yet when we are together I am only fabulous.  No pressure, fun, energetic, just letting things be and progress naturally.  Still I notice a subtle withdrawing from him.  Can you tell me if I am doing something wrong?  I have been working so hard to do it all correctly.  Reading Rory Ray and Christian Carter books and seeking therapy after my divorce.  I feel really good about myself but this uncertain relationship leaves me doubting myself.


Hi Julie,

Thanks for reaching out to me. I can appreciate how difficult it can be to make sense of men, dating and relationships, especially after a divorce. When a marriage ends, dating can seem like a foreign country!

It sounds like you have some insecurity in your new relationship. Seems like it’s possibly your anxiety stemming from an certainty about how your new guy feels about you, especially when you’re away from him.

The first thing you need to know is that you can’t control anyone but yourself. 

So, stop trying to read his mind or control how he feels. Your anxiety can also become a repellant to him. He could perceive it as neediness, and want to run the other way.

Take a deep breath.

Focus on what you CAN control.

You CAN control what you say and don’t say to him. You CAN control your behavior when you’re together. And from your email, I am sensing that you might be doing things on your dates that could sabotage the relationship.

You say you are ‘fabulous’ when you’re together. It seems to me, Julie, that you might be trying too hard to be the ‘perfect’ girlfriend, and you may be doing this at a big risk, especially if it’s not what you really feel inside.

Remember not to lose your SELF in the relationship.

This is tricky to navigate, especially if you are trying to get dating/relationships ‘right’ this time around. One of your dating gurus, Rori Raye, says that you should practice feminine energy, being the receiver in the relationship. I agree.

But that doesn’t mean being a pushover. It doesn’t mean being powerless. Quite the opposite.

In a healthy relationship, you’re loved for your whole self. Which means you’re comfortable asserting your own needs. It’s not easy for most people. It’s definitely a skill that I’ve learned over many years.

If you’re not comfortable sharing how you feel with a man, especially when feelings are hurt or when you’re confused by his actions, know that you’re not alone. And also understand that these are skills you can learn.

To learn more about this important topic, please listen to my latest radio interview with Rachel DeAlto about asserting your needs to a man in a compassionate way.

You don’t want to be nagging, pushing, pleading, or coming across as needy.

You DO want to have standards. Strong men like a woman with standards. If you’re too much of the ‘everything is breezy’ girl when you’re with him, especially if deep inside you’re hurting, you’ll soon feel disconnected from yourself and unsafe in the relationship.

When you feel safe with a man, you’ll begin to feel more comfortable asserting your needs and validating and listening to his needs.

Julie, this is an exciting chapter of your life. There is possibility and hope, and you are doing so much to support learning new ways of being with men. You are way ahead of most people!

Just remember to stay true to your authentic self throughout. When you tap more fully into your feminine energy, being the receiver, you’ll also need to learn trust and patience.

If you’re the type of woman who gave up on a man and did everything yourself in your marriage, this softening to allowing love in can be challenging.

Try and be patient as you allow men to take charge. He makes the first moves; ask you out, first kiss, courts you, pays for meals ~ you say yes (if that’s what you want, of course).

But remember to also say ‘no’ when you feel like it’s a ‘no’ (like no sex before monogamy, no to giving up your life to mold yourself to a man, etc.)

The more aligned you are with your true self, the more true your relationships will be.

Love will come your way.

Be compassionate with yourself as you learn to navigate this new dating world. It’s a lot of fun to go out with men and it’s the best way to learn about yourself.

Enjoy the journey, and the destination will come up to greet you.

Please leave a comment below and let me know if any of this resonated for you.






  1. Sandy thank you for your help. Everything you said is exactly what I needed to hear. It is nice to know what I have been reading hasn’t been in vain :-). I will work on the thing I can control, myself and work on not worrying about what I can’t control. Hmmm sounds so familiar… Like the serenity prayer! I was told to just “be” but it has been just a foreign concept, yet I think I am beginning to understand what it means. To be content in who I am and in my circumstances and not try to manipulate the outcomes to be what I think they should be, but instead allow them to become what they are meant to be. If I am close please let me know.


  2. Hey Julie,

    So glad you found my comments useful. And yes, my dating philosophy is similar to the serenity prayer. There is a lot of wisdom in that prayer. I find that many coaches tell people things like ‘get over yourself and move forward’ or like you said, ‘just be’. These concepts are complex and require doing internal work.

    There are specific steps that help a person get to that zen state of dating, living in that balance of showing up fully in every relationship, where you are fully expressed, you don’t do anything that feels out of alignment with who you are, AND you don’t twist yourself into morphing into someone you’re not to ‘get the guy’. That’s manipulation, and any relationship built on a false foundation will crumble.

    Those are some of the ways I support my clients. Having a coach in your camp cheering you through the dating process, especially when it feels hard and/or hopeless, can be a helpful thing.

    You never have to be alone, Julie. Feel free to reach out whenever you feel the need. Contact me if you’d like a complimentary 1/2 hour consultation to explore what a more personal, one-on-one phone coaching would contribute to your life.


Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.