Imperfection Does Not Equal Dating Rejection

Are you perfect?

Do you know anyone who is?

Look at the people you know who are in midlife or older: do you know anyone who doesn’t have some rough times behind her or is not currently facing some life challenge?

It’s doubtful—because you are in real life and not the movies! All grownups have some less-than-flattering “stuff.”

I received an email recently from Lisa, a woman who, after describing her life situation, asked: “Is there any hope for me?” Ugh. I can’t tell you how sad this makes me feel.

I’m sharing her letter with you in hopes that you – with your physical shortcomings, financial struggles and family dramas – realize that these are just parts of you; they don’t define you.

You’ll get some tips on how to manage this when you’re dating as well as the value of showing yourself the same understanding and compassion you show others.

Read Lisa’s letter and my response

Hi Bobbi,

I have a question. Here is my situation. I’m 42 years old, going thru a divorce and bankruptcy (thanks to my husband) and will have to eventually move in with my mom. I also have a child with autism.

I know I am a good person and I’m friendly, but eventually when I start dating all this is bound to come up. I think I will scare off any guy with all this crap I’ve gone thru. Guys are going to think I’m a loser. Is there any hope for me?




Hi Lisa,

A RESOUNDING YES!! There is absolutely hope for you!

We are all imperfect. We all have “stuff,” and grownup men – the confident and kind ones I hope you’re going for – know and accept that. They’re looking for a woman who is real.

Do you know anyone over 30 who doesn’t have something about her that, when put under a microscope, can be considered a negative? That person doesn’t exist.

As it relates to dating, the key here is how you present and manage your stuff. Context is everything when you share things of this nature with new men you meet.

Do my bushel basket exercise: Imagine yourself holding a huge basket. As you get to know someone, what you learn goes into the basket: he showed up on time, you like his shoes, he’s smart, his humor meshes with yours, and you share values and beliefs about life. Piece by piece, this information fills your basket, and that creates your opinion of that man.

Okay…your basket holds a bunch of good things. Now, throw in a tidbit or two that aren’t so attractive. He has a difficult relationship with his ex and mentions he has high blood pressure.

Add those two things to your already-brimming basket and mix it all together. Are you considering him as a potential mate? Will you try to continue to get to know him? Unless one of his “tidbits” is one of your absolute deal breakers…probably so. He has a lot going for him.

Now rewind and let’s start over. Imagine you just met him, and your basket only contains a couple of things in it: he showed up on time, and you like his shoes. Now throw in those tidbits: the scary ex and crappy health. That’s all you know.

Deciding he’s not for you? Are you trying to figure out how to escape the date? Probably so. He seems like a loser.

Got it? Perspective is a powerful thing.

Lisa, you are obviously a smart, friendly, loyal, very good person who nurtures and cares deeply for the people you love. Those are super attractive qualities, especially to men!

When you date, give him a sense of that lovely, kind and caring woman. Let him fill his basket with that on your first date or two. Then, if you decide to continue getting to know each other, you’ll start sharing more. That will include not just the scary stuff but also how gracefully and intelligently you are managing your challenges.

This isn’t about manipulation or lying or expecting people to simply ignore your (perceived) imperfections. It’s about learning how to see and accept yourself in a full light, and then putting your best foot forward.

You have challenges and you will get through them. As long as you keep learning and moving forward, and are willing to let a man help you when the time is right, you will find the man who will love to do it!

Congratulations on reaching out, Lisa. (That was the “smart” part I mentioned earlier.)

Keep reading my stuff and let me know when you’re ready to get to work on making this grownup love thing a reality.

With love,


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