relationship insecurityDear Sandy,

I am new to dating after my divorce, 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, etc. Yet when we are together, I am only fabulous. No pressure, fun, energetic, just letting things be and progress naturally.  Still I notice that he’s subtly withdrawing from me.  Can you tell me if I am doing something wrong?  I have been working so hard to do it all correctly. I feel really good about myself, but this uncertain relationship leaves me doubting myself.


Hi Julie,

It can be difficult to make sense of men, dating and relationships, especially after a divorce. Dating can feel like visiting a foreign country. There’s a lot to sort through in terms of forging a healthy relationship this time around.

You describe your insecurity and concern about how your new guy feels about you, especially when you’re away from him.

In a healthy relationship, you can usually sense how a man feels about you. You don’t have to guess. He’ll show you with his actions. He’ll escalate the relationship, from first date to weekly dates, from first phone call to daily calls. He’ll express how much he cares for you. Relationships should not be a guessing game.

You say you are “fabulous” when you’re together, but it seems to me that you might be trying too hard to be the “perfect” girlfriend. And you may be doing this at a big risk, especially if you’re not expressing what you really feel inside.

Remember not to lose your self in any relationship. You should not give up your needs or become a pushover for anyone. You should not give up your power or become bland and malleable only to his needs, without paying attention to your own.

Were your past relationships with men who negated your needs? Perhaps you were married to the type of guy who didn’t listen to or support you. Eventually you may have stopped asking for what you needed, and bore the burden of the entire relationship. You lost the ability to trust a man to be there for you. Learning to trust again can be challenging. But it’s crucial to being in a healthy relationship in the second half of your life.

In a thriving relationship, you’re loved and appreciated for your whole self. That means that you’re comfortable asserting your needs. I realize this is not easy for most people. It’s a skill that I’ve worked hard at and have been learning (and now teaching) for many years.

In this radio interview, I discuss Confrontation in Dating – Avoiding the Fight, but Being Heard. You’ll learn how to assert your needs so you’ll be honored and respected by men (and everyone else in your life). Please listen to the interview and pay attention to the communication skills I share.

You don’t want to be nagging, pushing, pleading or coming across as needy. But you do want to have standards. A good guy will be attracted to a woman who knows her standards. If you’re too much of the “everything is breezy” girl when you’re with him, especially if deep inside you’re hurting and stuffing your emotions, you’ll soon feel disconnected from yourself and unsafe in any relationship.

When you do feel safe with a man, you’ll begin to feel more comfortable asserting your needs. You’ll also be better at validating and listening to his needs.

Julie, this is an exciting chapter of your life, filled with possibility and hope. You are learning what it takes to be in a successful relationship with a man. You are way ahead of most people!

Remember that the more aligned you are with your true self, the more loving and real your relationships will be. Be compassionate with yourself as you learn to navigate this new dating world. Enjoy the journey, and love will come your way.

Wishing you lots of love,


For more midlife dating advice and a copy of my FREE report, “The Top Three Mistakes Midlife Daters Make (and how to turn them around to find love now)” please click here.

For exclusive articles and tips on dating, relating and mating in midlife & updates on my weekly radio show, please ‘like’ my Facebook page.

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