Will He Ever Ask Me Out? Understanding Men

Will he ever ask me out? I see this guy in our sports league and parties. He sticks with me when he sees me but, doesn’t ask me out. Will he come around?

will he ever ask me outShe’s Wondering, “Will He Ever Ask Me Out?”

“Dear Dating Coach Ronnie,

I know a guy through a sports league and we got close over the summer (he’s 44 and I’m 43). We haven’t gone out on ‘dates’ but would see each other at volleyball and end up staying later than everyone else, just the two of us having drinks.

We had great conversations and have a lot in common. Nothing intimate happened for a couple months. We have many mutual friends so we end up at the same parties and get togethers. If he knows I’m going to be there, he will be there and ensure we end the night together.

He mentioned a while back that he didn’t think he was ready for anything serious. I told him I was looking for more of an emotional connection with someone. A few weeks later, we ended up sleeping together.  He texted me the following night to ask me about how my team did that day.

He doesn’t text me very often. It seems like he needs liquid courage to do so. If I text him he responds. He engages on my Facebook page regularly and didn’t do this before we were intimate.

Pushy Women Take Charge

His last relationship ended in February and he said she was pushy and controlling. His prior marriage was with a pushy woman as well so I haven’t initiated contact much. I really want this man to ask me out. I’m not sure if he’s being cautious because of his relationships or if he isn’t into me like I thought he was.

I would think that if all he wanted was sex he would disappear after he got it. While he does pop up here and there, he doesn’t make a move. I think he wants me to pursue him because that’s what he is used to.

My gut tells me not to pursue. I’m wondering if a man sometimes takes more than a week or two to sort out his feelings, especially if he didn’t think he was ready for anything serious. I feel he does like me and is attracted. What are the chances he’ll come around and ask me out and how long might that take?

Please help!
Hopeful in Hartford”


Hi Hopeful,

Men are easier to understand than you might think. You just have to know how to “read between the lines” of what they say and do.This is one of my specialties – radically simplifying how to understand men.

He Doesn’t Want a Relationship

First and most important he told you he did NOT want a relationship. When a man says this PAY ATTENTION BECAUSE HE MEANS IT. Believe it for this guy and believe it any time you hear this in the future. Men never say this if they don’t mean it. It’s the most honest thing he’s probably said to you.

So, not taking the next step to ask you out isn’t because he’s cautious or doesn’t like you enough, he just doesn’t want to have a relationship and that’s often what dates lead to. It’s so much easier to just bump into you and let it just be something that happens.

Don’t Pursue Men

You say he’s used to pushy women. That’s because he rather not be responsible for what happens. This explains why you’re getting the feeling he wants you to pursue him. He can then absolve himself and say, “Hey, I told her I didn’t want a relationship but, she pursued me.” That’s why you are SO SMART NOT to DO IT. Don’t pursue men – it only leads to heartbreak.

He’s Not Emotionally Available

He might be stunted emotionally – maybe for life, maybe just for a while. But here’s the most crucial question of all – how long are you willing to wait for a man like that? He is not whole – something is missing or not completely right. He may be a great person and a great guy, but that doesn’t mean he’d be great in relationship.

Attraction is NOT Enough

I’m not saying he doesn’t like you. I’m sure he does like you and is attracted or he wouldn’t stick by your side or sleep with you. But you want more than a man who finds you attractive – you want a relationship that lasts and deepens and he’s simply not capable.

Missing the Essential Element for a Healthy Relationship

Yes, there is plenty you like about him. But he’s missing the most essential element for a man you want to be in relationship with – DESIRE for a relationship. He doesn’t want it or he would do something about it. To make you “his”. This is why he bumps into you rather than scheduling dates.

Sadly there is absolutely NOTHING you can do because he needs healing and only he can take the needed steps.

Here’s What You Can Do

The best thing you can do is come to grips with reality of the situation and who he really is. Have the self respect and awareness to recognize a lost cause. Rely on your own emotional maturity and skills for self-preservation to let go and move on.

There are other, better men out there who do want a relationship. Please go find one. I’m so very sorry to say this guy will never make you happy because he CAN’T. The answer to your question, “Will he ever ask me out?” sadly is NO.





Single for too long, Ronnie wanted to find love. So, she made a few tweaks and then dated 30 men in 15 months to meet her adorable husband Paul. Discovering the keys to midlife dating, she founded It’s Never Too Late for Love to help other smart, successful women find love too! Her mission is to share her proven dating advice  and keen insights about men with women everywhere who are serious about finding love with the right man. Ronnie Ann Ryan, MBA, CCC is a Certified Coach who has helped 1,000’s of midlife women with her Love & Dating Coach services. She’s been featured on BBC’s 5 Live Radio, NBC, ABC, and Fox News, NPR, eHarmony, MSN.com, MORE.com, Connecticut Magazine among others around the world. An established author, you can find her 6 books on Amazon.

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