Should I Waste My Time Meeting or Dating an “Imperfect” Guy?


Should I Waste My Time Meeting or Dating an “Imperfect” Guy?

(If you don’t feel like this now, trust me, if you start being aware of these things, and take better care of YOU in the dating process, you will become a confident woman in dating. For now, fake it till you make it.)

Instead, I would have rather that you responded with something like: That’s a very intuitive observation! Yes, that’s what I’m looking for. Hope you fit the bill! (This compliments him…then confidently tells him what you want for yourself.)


Natalie, the only waste of time is saying “no” to men because of superficial criteria or prejudging. Let’s face it: very few of us who are “well over 40? and dating have hundreds of men to choose from. We should grab our opportunities and see where we can take them.

Every date is a chance to find love, or at least a nice companion. At minimum it’s a chance to practice so you can get closer to it. I encourage you to:

1. Revisit your list and decide what you truly must have and if what you want is realistic. If you want a full head of hair, and you’re dating 60 year olds…good luck with that! You just decreased your chances of finding “your perfect man” by about 70%. (A guess.)

2. Remember that you know very little about these men you are meeting, so being flexible with your judgments will serve you well. Spend more time with them – get that first and maybe the second date – and then start comparing him against your (newly created) list.

Congratulations and a big atta girl for actively getting out there and working toward your dating and relationship goals. Remember to have fun, and that kindness and rational thought can be your best friends.

I encourage you to keep reading my blog, and reach out if I can further support you through with one of my coaching programs.

Let me know how it goes!

You have my love and support,



Hi Bobbi,

Thanks for getting back to me so quickly. I DO appreciate the input. Sometimes I feel like a 15 year old going out on a date!

Your advice and support makes me feel like I have my own private teacher and cheerleader. That’s exactly what I need to be able to get out there feeling that confidence and going for it!

Thank you, from the bottom of my heart,


As a final note: One of the best books on this topic is Lori Gottleib’s Marry Him: The Case for Settling for Mr. Good Enough. Yah, the title can freak a single girl out. But she does a great job at helping us understand how to become a “good picker.”

Article contributed by
Advanced Member

Bobbi Palmer

Dating Coach

The Dating and Relationship Coach for Women over 40 and founder of Date LIke a Grownup.
Register for Bobbi's free monthly webcasts Grownup Girls' Night Out: Let's Talk About Men! where she gives you tips and tools about dating, sex, relationships and more!


Location: Long Beach, CA
Credentials: Other
Specialties: Communication Problems, Dating/Being Single Support, Empowering Women, Wellness
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