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. Hey Ronnie,

    You’re so sharp and I’ve learned a lot from reading your posts. For me, I realized I was taking a lot of initiative texting with the guy I’m interested in. We talk online and he is away for work in another state and was able to get time off for the holidays to come to his home state (where I live). Through text, phone calls, video calls it is a 50:50 convo or him leading. He flirts and asks me of my plans in advance before he comes home. But he never asks me out. When he stopped communicating for a while, he reached back out, apologized and let me know he was struggling with personal things. I’m going to pull back initiating communication, but do you think he is waiting to see if I’m interested in him? I’m not the best flirt and can work on my charm. But I always reach out so I show interest in speaking with him. I’m concerned that my initiating communication but not asking him out has sent a wrong message. I’m definitly going to let him take the lead from now on but is it possible to make the transition? What are your thoughts?

    • Hi Peacelolly, First thanks for the compliment. Here’s the sraight-talk about this guy – talk is CHEAP and he’s stringing you along. If he really wanted to meet you, he would have done so already. Men don’t hold back if they are genuinely interested. I’m glad to hear you are going to hold back. Good – stop initiating! Just remember it doesn’t matter who leads the conversation – the only thing that matters is his ACTIONS. What has he done to SEE YOU and spend time together? Nothing! Just excuses. Dealing with personal issues lets you know he’s not relationship ready. He knows you are interested because you spend time talking to him. You do not need to ask a man out or ask to see him for him to know you want to meet. HE KNOWS this yet, does nothing to make it happen. So I’m sorry to be the one o tell you this but, that is EVERYTHING you need to know to realize he’s wasting your time and not the right man for you.

  2. Last week I asked a man I like out to coffee. He very happily accepted. I saw him tonight at a place where I had to be. He looked at me, and I was perplexed as to why he didn’t smile since he did with the invite. But I decided to ignore that and share some good news about me, I started out with holding my hands out counting, he came right over, and that was when the flood gates opened. I began sharing and he began smiling, opened up his arms inviting me into them, and warmly hugged me. I just wondered what that was about because at first when he saw me he said nothing. Maybe it was just my insecurity thinking that he changed his mind about our coffee coming up. I don’t know.

    • Hi Etta, I don’t know either! You bumped into to him or was that your date? I couldn’t figure that out by what you wrote. So if you bumped into him – he was probably surprised. And if that was your date, he might have been nervous. Who can say? As long as he warmed up, that’s all that matters.

  3. Hi Ronnie,

    I met this guy a month ago through online dating app. First date was just okay. He asked for a 2nd date on the first and it went better. He asked for a 3rd date before the 2nd date ended and took me on a fishing trip spending the day together. I invited him to my event the next week but he cancelled. Didn’t seen him for 2 weeks, then asked me for coffee before going out of the country for work. It’s been two weeks and his response through sms is not fast. He’s leaving again for the holidays and I want to see him and give him my gift before he leaves. But I do not know if he’s still interested. Hard to read in between the lines. He explained to me at coffee that he doesn’t respond quickly to texts because of work demands. He hopes I understand and wants to get to know each other better. I’m confused because I might be overdoing it by giving him a gift for Christmas or is that okay? Thank you, Emily

    • Hi Emily,
      Yes, giving a gift is premature when you don’t know how he feels about you. Hold off on gift giving until you’ve been dating a while (more than 3-4 dates). I can see why you are confused because he did ask for the next date during a date – normally that would seem promising. And, he did spend an entire day with you, but then reverted back to coffee. That’s just backwards! So, I think he’s showing you that he doesn’t like you enough to find time to see you or respond. Since he let weeks go by in between dates, the factual way to look at this is to see he’s just not that into you. Or he’s too busy and that means he’s not relationship ready. Either way, it’s time to find a new guy – one who not only wants to see you but can find the time. I’m so sorry to say this is NOT the guy.

  4. Hi Ronnie, I have a dilemma and loved your replies so thought you could advise me. I have met this guy on a dating site and have been talking daily by texts and calls. It’s been 5 months and we’ve become comfortable and he acts like he is my bf. The problem is he is not seeing me. Because of the circumstances we haven’t been on a date for 4 months. Now in the same city for more than a month, he still hasn’t ask me out. I couldn’t wait so asked him out, he said yes, but didn’t take any initiative after that. I really like this guy and we have great chemistry. Now it is clear that I’m pursuing him because I often text first, but he’s the one who calls. So I convinced myself it’s a balanced win-win. So why is he not seeing me. Is he intimated by me? Afraid of meeting the real me or just not that into me? Should I continue talking and waiting for him to ask me out, pull back or just ghost on him? It would be great if you could really help me out here. Thanks a lot.

    • Hi Oindrila, If it’s been 5 months and you’ve never met – that man does not want to meet you. Sadly he is probably already in a relationship or he doesn’t want one. Maybe he is not who he says he is. No need to wait longer or pull back hoping. Stop communicating with him and block him because he is just wasting your time. I’m sure you will miss him but this is not real. So you are robbing yourself of finding true love by sticking with him. Do yourself a favor and let him go. In the future, do not text longer than 7 days without meeting. No dates, no texting or calling. That will keep this from happening again. men who make excuses about why they can’t meet are not to be trusted. Work is the most often used excuse because men know you won’t question his need to work. Read this post on texting to get really clear on virtual relationships.

  5. Hello,
    What if you have already made these mistakes? Is there any way of bouncing back? If the only advantage is waiting and letting him pursue is there a way of turning it around after the mistake?

    • Hi Nena,
      If you’ve been pursuing a man, the best thing to do is stop even if you’ve already been on several dates. Give him the space to step up so you can see if he’s just going along for the ride or he is actually interested. Believe me, if he’s interested and you stop asking him out – HE WILL CONTACT YOU. At the very least he’ll be curious. So if he calls to ask where you’ve been do NOT say you were holding out to see what he’d do. Just say you got busy. Then if he’s really into you, that’s his chance to ask you out and prove his worth!

  6. Hi Ronnie, your views are really helpful. What are your thoughts about my situation? About 2.5 years ago I met a man on okcupid who was in an open relationship. His intentions were clear and I was not looking for anything serious. We hit it off and dated for 7 months and eventually feelings on both sides developed. I didn’t want to get hurt so I broke it off. I dated other men but could not get this one out of my mind. So I contacted him after 6 months and we’ve kept contact since then. I tried to see him, but he said he was too busy. I didn’t believe his excuse of course, but as I enjoyed the contact and effort was 50/50, I decided to keep the lines open. He complimented me regularly (just words, I know) and I assume that my interest stroked his ego. A month ago he agreed to a date. We had fun, the connection was still fluid. He told me his wife filed for divorce but he had tested positive for hpv. I was confused afterwards. He kept complimenting me and I wanted to know how he really felt about me so I decided to escalate by telling him I still want him. His response was that he was surprised and I took that as a rejection. I haven’t responded and we haven’t talked in 3 weeks now versus our almost daily contact. Do you think I’m right by assuming that I came on too strong and that he doesn’t want anything more?

    • Hi Svetlana,
      My bet is he wasn’t really interested again – his excuse “I’m too busy” is the clue. You persisted so he gave in. But when you let him know you wanted him, he disappeared because he doesn’t want anything serious. He didn’t have exclusivity in his marriage so why would he want that now? While I encourage women to not express their feelings first because that is coming on too strong, in this case it looks like you did yourself a favor since he showed his true colors.

      Here’s what I hope you’ll do next…discover how to value yourself more than putting it all on the line for a cheating man with an std who isn’t yet divorced. Who knows if his wife knew they had an open marriage? That was likely a lie. You deserve a man who is honest, loyal and loving. This man had something that caught your attention but he was never truly available. The best dating strategy if you want a serious relationship is to go for serious from the start. It’s super rare to change a man from casual to exclusive and long-term. Love yourself enough to go for what you want with a better man.

  7. Thanks Ronnie, I was really stressed after I met a guy who had everything I’ve been wanting. But I rushed and played his role – even gave him a gift. Well I have lost the guy because I called him several times and even cooked at my place before even taking time to know him. I feel bad but its done

    • Don’t feel too badly – it was an opportunity to learn and next time you’ll do better right? Just don’t repeat the same mistakes and you’ll be fine.

  8. Hi Ronnie,

    I’ve met a guy online, we texted for a week before he asked me out, the first date went way better than I’ve expected and I felt like we really hit it off. He texted me shortly afterwards if I got home safe,etc. We scheduled a date for yesterday kinda last minute because I’m going on a trip for 10 days. The thing is he didn’t contact me yet, the date was only yesterday, so obviously he still can text me but I’ve been wondering if I should text him first to show him that I am indeed interested since he is the one who initiates conversations all the time. The other thing is that he didn’t even try to hold my hand or anything, is this any kinda sign or he is just taking things slow and really wants to get to know me? What do you think?
    He is a gentleman, he said the same thing after both dates: “talk to you later” with a kiss on my cheek.
    I really like him and that is why I don’t want to come off too eager and as you said make him run away, so what would be the clever thing to do? I’am fairly new in the dating world..

    Thanks a lot!

    • Hi Evie,
      You can text him one time first but don’t do it often. You can thank him for a nice time (did he plan the date and pay?). Hopefully he will contact you upon your return. don’t fret – remember if it’s not him, it might be the next guy. This is something you cannot control so you might as well relax and see what happens.

  9. Hi Ronnie,

    I read your book about how to spot mr wrong last night in one go and it really made me feel more confident, I realised how I dated a few of these men and put my effort and energies into relationships that clearly were not going to work..I dated for a year Mr narcissist and Mr nurse, a selfish man that would need lots from me but never gave anything in return and only was interested in talking about himself..this was since the very first date! I wish I had read your book back then, I would have probably saved lot of pain..but instead I decided to help this guy and fix him! I ended up without energy after a year and with low self esteem, thank God my friends and family supported me to regain my self worth.. I want to read your other books as well, I think it is good to have very clear in your mind what you want and you’re looking for and not put up with certain things from the beginning because things will never get better than that. Thanks a lot Ronnie 🙂

    • Wow Scarlett! Glad you found my newest book Is He The One? helpful. You certainly goggled up the info which is great. Arm yourself with info – the more you know about men and dating in midlife (or at any age really), the better your chances of finding the right man for you.

  10. I stumbled upon this website while googling whether or not it’s a good idea to go on a weekend trip with someone after two very excellent dates. While I didn’t find my answer here, I found very tried and true advice from Ronnie.

    I just wanted to extend a huge THANK YOU for giving sound and sensible advice to women (and men)…and an even bigger thank you for following up to almost all of the questions. This information is beyond valuable and I’m glad someone out there still stresses the importance of femininity and gender-roles.


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