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

30 minutes. That’s about how long you generally have to “get to know” a man before deciding to have a cup of coffee or date with him. You meet online, or at the local bank, and that’s about it.

But he seems imperfect. He’s clearly missing one of your must-haves. Should you gracefully decline? After all, you have very little time to waste, right?

We all have a list, or at least a vision of the perfect guy. He’s probably hysterically funny, always interested in your happiness, openly shows that you rock his world, and shares your love of [art, music, astronomy, etc.] Oh, and I’m sure he’s taller than you.

When you have a chance to meet a guy, but he sure doesn’t seem like all that, is it a waste of time?

One of my blog readers sent me an email asking that question. I hear forms of this so often, so I thought I’d share our emails. Please read on if you find that the men you’re meeting aren’t living up to your standards.


Hi Bobbi,

I answered an email from a guy on Plenty of He met all my minimum requirements ie: he contacted first, nice, not too long or mushy email, commented on my smile and what it showed of my characteristics. I was impressed. I’m going out with him even though he’s not as tall as I like (he’s 5’7 as am I and hopefully he’s not stretching it!).

He wrote that it seemed I was looking for someone special and not a “one night stand.” I responded by saying he was right on with his assumptions. I told him if after that he’s still interested let me know and I will give him my number.

He replied that he was still interested and I gave him my number, He didn’t call for about 4 or 5 days but sent me a message through the website saying he was sorry he didn’t call and soon as he got a breather from work he would call. He finally called last night and we set up a meeting for Friday (for a drink) at 6:45pm.

I  know it’s just a meeting, but just need your expert opinion: I’m not too impressed that he took so long to call. And he is 42 and I am 51. Am I wasting my time?

Thanks so much,



Hi Natalie:

In a word: NO. Age really isn’t that important. Life experience and lifestyle are what usually end up counting.

I know a lot of us have “rules” about age; but I encourage my coaching clients to be open about this. Especially at our ages. My husband is 10 years older than I. He was out of my search range, but here I am, happy as a clam. (Thank goodness he didn’t care!)

Doesn’t this man know your age? It obviously doesn’t bother him.

Don’t get too stuck on a guy not calling right away. For many of them, until they meet you they feel they have no skin in the game. (Unlike us who can imagine ourselves married to a piece of paper.)

It’s pretty easy to slide you aside because he doesn’t even know you. It has nothing to do with you. And don’t think it measures his interest in any meaningful way. How many guys have shown great interest and then dumped ya like a hot potata? So don’t put much emphasis on this beginning part when it comes to the order in which he meets you. It’s what happens after that counts.

And, Natalie, I know you didn’t ask, but I have a little more advice:

I want none of that “if you’re still interested” stuff! That is something that comes from a woman who is insecure and apologetic about asking for what she wants. You are neither. (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.”

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