I Don’t Want to Chase Him, But He Doesn’t Initiate!

Don’t Chase Men

Dear Ronnie the Dating Coach for Women over 40,

I have an interest for this guy who also works for the same company, but in a different building. He’s tall, dark and handsome, just the way I like them. The only thing is, he is really shy. We have gone for coffee and it went well, but I don’t think he is looking for the same thing I am.

I want a relationship and marriage. I don’t know what he thinks of me and I am not sure he likes me or finds me attractive. I am curvy and sometimes men don’t like that. So, my question is, how do I get to know how he feels or what he thinks without scaring him? I don’t want to chase him like I’ve done in the past with other guys. But, it seems that if I don’t initiate an email or phone call, I never hear from him.

Tired of Waiting in WA

Hi Tired of Waiting,

As a dating coach for women, I share my insights and knowledge collected from 9 years doing this work, reading everything in sight and working with thousands of people. It is from this place that I can tell you, if a man is interested, if he likes you , if he wants to date you, he will do what is necessary to make that happen.

In other words, there is really nothing you can do to find out if Mr. AtWork likes you. Truth is, there is nothing going on. If he wanted to date you, he would pursue you. It’s that simple. Yes, there are shy men, but they also know what to do. Like Greg Berhandt says in his best selling book, “He’s just not that into you.”

He is probably a nice guy, so when you text or call, he does respond. But he never takes up the initiative or starts anything on his own. This is your clear signal to move on.

Since you went for coffee with him, and he hasn’t followed up, I recommend moving on. Look to connect with other men who are more motivated to date, more interested in you, or BOTH!

There are so many great single guys out there. Build up your flirting skills, smile and be friendly. Men are everywhere and there is definitely more than one good man who will find you attractive and be a good match. Please don’t waste time on the wrong guy.

Wishing you love,


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.

22 thoughts on “I Don’t Want to Chase Him, But He Doesn’t Initiate!”

  1. I have a guy friend and we work together. I developed feeling for him. One day I got a message from work concerning Covid-19 and the lay-off so I sent him a message on Instagram letting him know. When he responded he told me to stay close and keep in touch. We both work for a professional sports team and he lives in another state during the off season. He asked if I would pray for him while he traveled back to his home town. What does that all mean?

    • Hey MDT, What does it mean? Not much in terms of romance. It’s one of those things people say. Maybe a tiny bit flirty but minimally. If he meant anything by it, he’d be the one to keep in touch. I’m assuming he’s not staying in touch though right? So that is all you need to know about his romantic intentions. He probably likes you and wishes you well, however that is nothing seriously romantic. A request for prayers? Again, sweet but nothing serious. If you would like a loving relationship, maybe it’s time for you to start looking for that locally!

  2. As a guy, I known several women I’m very friendly with. Even though they are my type, as we get to know each other, red flags come up that my make me think twice. One woman I could have dated, but in conversations I found out she has a “companion”. She’s not serious about him but he offers something to do and she stays with him frequently. I hardly initiate or ask her out. She’s told me the phone works 2 ways since she always calls or texts. She is a great woman, funny, smart and somebody I could see dating, BUT because of her companion, I keep my distance and stay friends. I don’t ask her about it because it’s not my place. Men pay attention to what women say and do and when it doesn’t add up, even if there are feelings, they prefer to keep a safe distance.Pursuing a woman who has his kind of man friend might signal her that you’re OK with it. Women, look at yourself to see if you could be doing something that throws a man off so he sticks to friendship.

    • Hi Alex, Thanks for sharing your insights – very interesting! My comment is that you need to be more open in your communication. You can certainly be direct and ask about the other man. You could even say, “I’d like to date you, but I know you are already seeing someone.” Then see what she says. If you start dating and things go well, you might win her over and can ask her to be exclusive. And you don’t need to worry about signaling her that it’s OK to date around, you can TALK about it. My question is: why spend time with women you like, but won’t date? If you want to find love, be more direct with women who you know are seeing other guys, or find a woman who isn’t dating around.

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