Don’t Pursue Him, Or You ‘ll Make Him Run

Don't Pursue Him
Running From Your Aggressive Moves

Here’s a little secret I don’t tell everybody…I have a few male dating coaching clients as well. I love coaching men because I learn so much about how they think to share with all of you!

Don’t Pursue Him – It’s a Big Mistake

Recently, my client, Ken, told me about a woman he just met online. The first date was on a Saturday night, lasted for about six hours and went very well. Ken found her to be a lot of fun to talk to and really enjoyed her company.  (Ken and I have some work to do because first dates should never last this long.)

Let me share background on Ken. He is a good looking guy in his 50’s. He’s practical, down-to-earth and easy to talk to.  This is a man who has done his healing after divorce and wants a long-term, loving, relationship with the right woman.

Since he liked Sandra a lot, he made a second date at the end of the first. He suggested getting together a week later on Sunday night, which Sandra was happy to accept.

Now, this is where the story gets bumpy. Apparently, Sandra is very hot on Ken. She is not managing her enthusiasm and letting the man lead during the initial courtship. Sandra made a series of what I call “Fatal Errors” that caused her to look over-eager and a little bit desperate. Here is my advice as a dating coach for women in midlife (or at any age really).

1. Don’t call him in the beginning
She couldn’t wait the eight days for the second date that Ken set up. So she took matters into her own hands and called him. Some men feel like you are invading their private space when you do this, so it’s a risk.

2. Don’t pursue him. Let him ask you out so you know he is interested.
While Sandra had Ken on the phone, she asked him out for Thursday night, creating her own second date. Ken’s a nice guy and frankly felt flattered. So he agreed to meet her Thursday.

3. Don’t buy men gifts!
When Ken arrived at the designated meeting place for date two, Sandra had not one but two gifts for him. They had talked about favorite books and wine, so she bought him one of each.

4. Don’t have marathon dates.
There is some driving distance between where Sandra and Ken live, so the dates have been longer than usual. Date two was also more than six hours.

You may think I am overreacting but I assure you that I AM NOT. This is what Ken said to me after the second date.

“Well now I have my third date in a week coming up. I’m not sure I want to spend that much time with her so quickly. She bought me gifts you know. Why did she do that? I mean it was nice and all, but I felt uncomfortable. I didn’t have anything to give her. It was awkward. I was flattered that she called and asked me out and I had a good time, but now it feels like too much to be seeing her again so soon. I just started dating online and want to meet other women, so now what do I do?”

In truth, Ken played a role in some of these mistakes.
– He didn’t keep the first date short.
– He accepted her date request rather than waiting.
– He didn’t go slow at first to avoid letting things get serious too quickly.

Single Gals, Please Hang Back and Let the Man Lead – You Can’t Go Wrong
Regardless of the mistakes Ken made, it’s your job as a woman to manage some of the dating mechanics. Please control your enthusiasm so you don’t appear over-anxious or worse – desperate. Don’t call men, try to speed things up or ask them out on dates in the beginning. And don’t buy them gifts for any reason, unless it’s a birthday, then get a token gift. This all boils down to the basic rule of thumb – don’t pursue him.

Don’t Lose the Only Advantage You Have!
Wait to see what a man will do of his own accord to win you over. If you do not do this, you lose the only advantage you have to observe his behavior and collect information about how interested he really is in you.

What Seems Like A Nice Thing Can Negatively Impact His Masculine Ego
The risk of you initiating is HUGE because you could make the guy uncomfortable and look elsewhere for women who make him feel good about his masculine energy or enhance it. That’s the problem!

If you pursue him, chase him, call him, ask him out and buy him gifts, you are USURPING HIS MASCULINE ENERGY and emasculating him. This will never help him feel good about you, so DON’T DO IT!

Learn from Sandra and Don’t Make These Aggressive Fatal Dating Errors
You want a good man to grow more attracted to you. Give him the space and time to pursue you and get invested in you. Men are slower to bond and there is nothing you can do to hurry this process for him. Your efforts to let him lead will usually be rewarded. But at the very least, you won’t send men away suspicious and worried that you like him too much too quickly – like the movie Fatal Attraction.


PS. If you’ve made this dating mistake, listen to my Free Audio Program 12 First Date Mistakes Women Make that Ruin Your Chance for Love.  Or schedule a Free 30-minute conversation with me to discover how coaching can help.





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,, and Connecticut Magazine among others. Also, Ronnie is the author of 6 books which are available on Amazon.

379 thoughts on “Don’t Pursue Him, Or You ‘ll Make Him Run”

  1. Hi, I met a guy online and we had an amazing date. He paid for everything and ordered and paid for a cab to get me home. Texted to make sure I was home and again the next morning. We arranged a second “provisional” lunch date a couple of days later but knew it may not happen as he was going away on business. He got tied up at work and it didn’t happen. He is now away on business. He texted from the airport and I replied enjoy your trip and great to catch up when you are back if he still wanted to. He said, “Of course”. That was two days ago and I feel ridiculous – like I’ve handed over all my power (which I struggle with) and I don’t know if I will hear from him. I’m already fearing he isn’t going to contact me and I want to reject him before he can reject me or go gushing in and tell him how much I want to see him again and push him away. How can I get the happy balance?

    • Hi Emma, The problem here is that in your mind, you are so attached you imagine you are already in a relationship. So that revs up the pain thinking about rejection. But you’ve had one date! So yes, you are absolutely giving your power away to a man you do not know at all. Time to reel it in. Say to yourself, this guy or someone better every time you start to freak out. Because you have no idea if he’s the one. Read the book Women Who Love Too Much which you will find very helpful.

  2. Hi Ronnie,

    I met this guy online and we’ve been on four nice dates. He’s been texting me just about every day. He has not called me. I’ve been letting him take the lead. We went out last Saturday night and it was great. He texted me that it was great. We have not slept together. We made plans to go out to see a movie this past Wednesday night. I got ready and he never showed up. I was surprised because everything has been going so well. I gave him the benefit of the doubt about missing the movie date. We are both 65 and it’s hard to meet someone at this age, it’s not like when you are younger. Anyway today we’ve been texting. I sent him a text asking if he would like to come to my house this evening. He’s been here once before. I felt comfortable asking him at this point. But here it is two hours later and he hasn’t answered my text. Should I move on??? Thank you and thank you for the great article!

    • Hi Diane, Yes, it’s time to move on, nothing else makes sense. Some men who are happy to see you from time to time but don’t stay in touch. Without calls between dates, there is no deepening of your relationship. Then he stood you up! Why would you ask him to your home when he treats you like that? I encourage you to improve your self-respect. There are more men online – plenty. Meet one new man a week until you find a good one who wants to be with you. Sadly, this man does not and has already shown his stripes.

  3. I prefer men to ask me out but I asked a guy out over the internet the other day. The reason was I happen to be in his area (another country) and I was going to leave the day after so I asked if he wanted to go for a coffee. He responded that he would love to and wanted to set up a date the week after but I responded a couple of days later that I no longer was there. Then he took the initiative suggesting another date if I was to return. I said I was going to return a couple of months later and we could try to meet then and he responded definitely. So have I ruined the prospective relationship with this guy now by taking the first step?

    • Hi Kris – No you didn’t ruin anything. This is completely different. I encourage women to not text longer than 7 days wit the apps and online dating. At that point if you want to meet, I suggest a short phone call 10-15 minute and then set a date. If he doesn’t ask you out, in this one case, you can ask him. It’s just a chemistry check, not a real date. Just don’t ask the same guy more than once. By the way, don’t put much stock in that kind of long distance relationship. He may be enthusiastic to see you again, but how often can you go there? Go, have fun and enjoy, but don’t get your heart set on that LD man.

  4. Hi Ronnie,
    Reading your post I realise I have been a Sandra with the guy I am currently seeing. We’ve been friends for few years now and started dating about 3 months ago. We’ve seen each other 7-8 times since and all seemed ok until a month ago. He’s been busy with work so I kept initiating contact and ask to reschedule dates (he cancelled twice). I only saw him once this month and it went well in my head but I started the Where are we going talk and he pulled off after the date. He cancelled again the coming weekend and I haven’t seen him for 2 weeks now. He would still call once or twice a week and text occasionally but no sign of rescheduling. I am trying hard not tto initiate that much contact myself. Did I lose him or is he taking some space?

    • Hi Sunny, Don’t blame yourself – you did what you thought was right at the time. But now that you know better, you have stopped initiating – good for you! Your question is, “Did you lose him or does he just need space?” Instead ask yourself – Why be emotionally attached to a man who cancels and is evasive? Is that how you think a man shows his love and appreciation for you? I hope not. For whatever reason, he is not showing you love.

      I encourage you to turn this situation around to see that you DESERVE a man who is captivated by who you are as a woman! If that were the case, you would clearly see HE IS NOT THE ONE FOR YOU. A man who cancels and pulls away is not worthy of your love and attention. It’s time to look for a better man.

  5. Hi Ronnie
    My boyfriend blocked me from every where. I didn’t do or say anything wrong. The only thing I asked was question where I stand in his life. The reason I questioned him because, he wasn’t the same anymore. He stopped texting me unless I texted first. He said “As u know I’m busy with work and life and I want some space.” I said okay but you’ve changed. He didn’t open my message so after few hrs I msg back asking “Is everything is okay?” I realized he blocked me, so I messaged him on Instagram and viber – he blocked me there too. I cant stop crying, I lost my appetite, I cant even sleep. I don’t know what to do? Should i text him from different number and ask him what i did wrong?

    • Hi Ela, I’m sorry you are so upset, but you need to accept this breakup and that he doesn’t want to talk to you. Stop contacting him and do not message him from another phone. He’s NEVER going to tell you what happened – if he was, he would have already told you. But that time has passed. He’s not interested. Maybe you didn’t do anything wrong, he just isn’t interested. You must RESPECT that even though he didn’t properly breakup with you. Then get some counseling. Time heals, but a therapist will help you regain your strength and confidence – essential to feel good about yourself and get your next boyfriend when you’re ready.

  6. Hi Ronnie,
    Your article is very helpful. I have a dilemma and would really appreciate your help. I really like this guy, and we both have been texting. It felt so natural and there was so much chemistry. However I now feel like he is “ghosting” me. He didn’t respond to my last message. Could I message him again?

    • Hi Kiera, I don’t mean to contradict you, but chemistry via texting is not really chemistry. This is in the fantasy stage. If you haven’t met him yet, I’m not so sure what the point is. Of course you can text him one more time. But keep in mind, a man who doesn’t ask you out on a date and then doesn’t respond to your text is not showing signs of genuine interest. No matter how good the connection feels, it’s not real without spending time face-to-face.

  7. Thank you so much Ronnie. I think you are right that maybe the life style is the major reason. We eventually talked on the phone yesterday and he thinks it is better to be friends since he does not see him to fit my active lifestyle. I am a type of girl who loves to hike in the mountains or canoe in the wilderness for days and weeks (it’s quite hard physically), but he is not interested in doing any exercise or engage in adventure. I really miss the time we were together. The conversation was so much fun. But I think Ronnie you are right that in the long run, we are not compatible. I know some adventurous friends’ husbands/boyfriends who do not do any activity. Their relationship still works. But somehow I also hope to find someone who enjoy the same activities like me. I feel sad that he decides to just be friends, but it’s time to move on!

  8. I have been dating a guy for 7 weeks and really like him. We see each other 2-3 times per week and do lots of activities (dinner, lunch, museums, art galleries, one ski trip, cafe, shopping, parks). After our last date (4 days ago), he suddenly pulled back (stopped calling/texting). We talked about our values and political views. My lifestyle is different from his – I’m very active with lots of outdoor activities on weekends and holidays. He mostly stays at home on weekends. I wonder if he pulled back because we have different values and life styles. I really enjoy time with him and he was always affectionate and caring. I don’t know what to do. In three years, this is the first time I’ve had more than 3 dates with one guy. Thank you for giving me some suggestions.

    • Hi Amy, It does sound like he re-evaluated once he realized how different the two of you are. Sadly, if he’s a stay at home guy and you like to be active, after a while you will become resentful. So even though it lasted 7 weeks, its seems this has run it’s course. The two of you are probably not compatible long term and better to know sooner rather than later. The good news is – since you got one guy interested, there will be another! Don’t think you are going back to nothing. You are starting again fresh and I hope you find a better match.

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