Understanding Men: What Am I Doing Wrong on Dates?

Want help understanding men because you aren’t getting more than 3 dates? These insights will put you on the right track for love.

Why Can’t I Get a Boyfriend?

“Dear Love Coach Ronnie,

First, thank you for all your advice and most of all that it is honest and straight forward.

I have a bit of a predicament. I’ve been online dating for over a year and had a lot of interest and dates. Some guys I felt a connection with, but my problem is I haven’t gone beyond three dates (with two of the guys) and most of them go quiet for no reason.

I’m left wondering what I have done wrong. That is really hard for me and I want to improve in the future.

For instance, I met a guy online in August and we were texting and in touch all the time, met up in September (he came to me, a plus for effort). We had a lovely afternoon date in a champagne bar and it was his treat.

About a week later he asked me when he could see me again and we agreed on that Saturday. Friday evening I sent a message to ask how he was doing, no reply and no date on the Saturday.

I consciously avoid being in touch all the time as I don’t want to be pushy. I did send him a message after complete silence for a day, saying that if he wants to stop what we have started, it’s fine by me. He replied, “I never said that” and then went silent again.

I have now given up contacting him, but here is the odd bit, he still goes to look at my profile on the dating website and this is confusing to me, is he interested or simply curious?

I would be very grateful for any help as this whole failing at dating is really affecting my confidence, and I am normally a very confident person. Thank you for shedding any kind of light on my dating issues as I am about to give up on trying to find a man.

Thanks Kindly,

Dear Kat,

Having been in your shoes, I do feel your pain and empathize. The dating process is confusing and so unclear when you are in the middle of things. That’s why I offer my dating  advice, from over here and having been down the road, I see things more objectively.

Understanding Men: It Might Not Be You

First, I want to reassure you that you are probably not doing anything wrong. Women tend to blame themselves thinking it must be them. You take on the blame easily but there is often no need. I dated 30 men in 15 months and all but three disappeared without a word after 1 – 3 dates. This is COMPLETELY NORMAL, to be expected and happens to most women.

Why does this happen? There are truly countless reasons, so it’s hard to know for sure, but here are some options for what might have happened with other guys:

  • You reminded him of his ex
  • He doesn’t know what he wants
  • He lost your number
  • He waited too long to call and then felt dumb
  • He liked you, but not enough
  • He thought you weren’t right for him
  • He didn’t feel the chemistry
  • He could tell you wanted something serious and he wanted casual
  • He met someone new, etc.

None of these reasons have much to do with you or anything you could or should change.

These Men Did You a Favor

I tell my dating coaching clients that there is another, more positive way to think about this. When a man opts out of your “dating pool,” he is doing you a favor by not wasting your time. He could have changed his mind after 3 or 6 months, but he figured out quickly that things weren’t going to work out for him. So he moved on. I recommend you do the same. I know how it seems that some of these guys should have worked out, but they didn’t. Let them go.

One Man Closer to the Right One for You

Since dating is a numbers game, meaning you have to date a lot of men often to find a good match, every man you date brings you one step closer to the right guy for you. This is another positive way to look at this situation because you just have no control over it.

Since you’ll never KNOW what  happened, make the best of it by realizing you are getting more experience and learning about what you do and don’t like. You are also getting to hone your dating skills and this CAN BUILD CONFIDENCE even if these men don’t continue to see you. Just keep reminding yourself that you are one man closer to your dream of love.

About Mr. Champagne

Why does he not cut you lose when you asked him a direct question? From everything I have learned it could be:

1) Men don’t like to hurt a woman’s feelings.
That’s why they disappear instead of saying, “I’m not going to call again.” Honestly, can you imagine a man saying that? Worse still is if he told you why, “I’m not going to call again because even though I find you attractive, your laugh is too annoying.”

Women often think they can simply be direct or ask a direct question. But the chances of you getting an honest answer are just about zero. They would rather run or disappear than bear the brunt of a possible emotional outburst.

2) He doesn’t know what he wants. That’s why he’d rather have you hang around as a possibility, until he can decide if you fit his image of the perfect woman

3) He needs the ego boost. Some men have highly bruised egos or a sadistic streak trying to get even with women and need lots of women “on the line” who text or call and hope he’ll pick them.

I’m sure there are other potential reasons and I could go on. That’s the thing about understanding men in these situations – it can’t be done. The same goes for women from a man’s perspective, trust me. We think differently and are wired differently.

Don’t Waste Time on Figuring Out “Why?”

Instead of wasting time trying to understand and wondering what you did wrong, think about what you learned and move on. Toss these dead end dates in the pile behind you. Hold your head high and move on knowing none of these men have been the right man for you. If any of them had been “The One” they’d never let you go. The right man for you will pursue you and stick around.

What If It Is You?

Okay, now what if it is something you did? Here are some things to think about, just in case there is room for improvement:

  • Did you talk about yourself negatively or put yourself down?
  • Did you complain about dating, men, your ex or past relationships?
  • Did you reveal any life challenges such as work, finances, health?
  • Were you upbeat and light-hearted or low energy and dull?
  • Were you fun to be with?
  • Did you have a checklist in your mind and interview the men to see if they “qualified” to date you?
  • Did you talk only about yourself or show interest in him?
  • Did you tell him how busy you are? (Men can be very sensitive about women who don’t have time for them.)
  • Did you talk about your important job?
  • Did you use your business skills (a no-no) or rely on your feminine charm?
  • Did you spill your guts about past relationships as if he was a therapist?

Think back to your most recent dates and honestly assess if you have done any of the above or maybe quite a few. If you have been making these innocent mistakes, now you can start to correct them. The listed behavioral errors can make you a lot less attractive. Some men are sensitive and gun shy. They may have been with women who were tough on them emotionally and now they are skittish. Or they know right away what will and won’t work for them.

I’ve given you a lot to think about towards better understanding men. But if you’d like a bit more, check out my audio program, It’s Not You, It’s Him

Wishing you love,

dating coach, find love, meet men









Single for too long, Ronnie wanted to find love. She put her skills from personal development and her spiritual path to work, dating 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to manifesting and midlife dating, she founded It’s Never Too Late to help smart, successful women find love or live an empowered and magical life. Ronnie Ann Ryan, MBA, CCC, is a Certified Coach who has helped 1,000s of midlife women with her Love & Magical Life Coach services. She’s the host of the Breathe Love & Magic podcast and has been featured on NBC, ABC, & Fox News, NPR, BBC, eHarmony, MSN.com, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

2 thoughts on “Understanding Men: What Am I Doing Wrong on Dates?”

  1. Hi Ronnie, Your advice to allow the man to pursue is spot-on. When you tell women, “if he’s interested, he will contact you” that is also accurate. The first man I dated post-divorce, to me, was a great fit. We dated for two months and then… nothing. He ghosted me as described. I was heartbroken. We had something that I thought was special and I never heard from him again. I blamed myself and wasted a ton of time “analyzing” what could have gone wrong. Can you imagine my surprise recently when this man contacted me out of the blue? It’s been more than TWO YEARS. When he reached out, I asked him what I could have done differently and guess what? He said NOTHING because it “wasn’t me.” Instead, he told me the “problem was all his” and he ran because he was scared since we made a strong connection so quickly. This has done more for my self-esteem than I could’ve imagined. It has erased all of my self-doubt and reminded me, as you say, the issue is not us and is usually the man. So, men can and DO come back, but only when you don’t pursue them and they have the time to think and realize they let the right one get away. Thanks, Healed Heart in Minnesota

    • Hi Jane – thanks for sharing your story! I’m glad things worked out for you. Not all men come back but it’s best to realize that if a man disappears, that makes him the wrong man. The right man for you would never leave or he does come back as in your case. Either way, you can’t wait around if you want to find love.

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