Will He Ever Ask Me Out? Should I Wait Or Ask Him Out?

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 he didn’t think he was ready for anything serious. I told him I was looking for an emotional connection with someone. I keep asking myself, will he ever ask me out? A few weeks later, we slept together.

He texted me the following night to ask how my team did that day. He doesn’t text often and it seems like he needs liquid courage to do so. If I text, he responds. Now he engages on my Facebook, but didn’t do this before we were intimate.

Pushy Women Take Charge


His last relationship, which ended in February, and his prior marriage were with pushy women, so I haven’t initiated contact much. I really want this man to ask me out. Is he being cautious because of past relationships or is he not into me like I thought?

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. Maybe 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. Will he ever ask me out? What are the chances he’ll take this step 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.

Pay Attention To What Men Say

First and most important, he told you he did NOT want a relationship. When a man says anything to push you away, PAY ATTENTION. This is his way of being upfront and honest. Believe him and believe it any time you hear this from a man in the future.

Simplify understanding men by believing any guy who says, “I don’t want a relationship. I don’t want to get involved. I don’t want anything serious.”

Men never say this if they don’t mean it. It’s the most honest thing he’s probably said to you. There could be any number of reasons he doesn’t want to get involved. He can’t handle it, he doesn’t want to be tied down, or he’s not emotionally available.

The Reasons Do Not Matter

Truth is, the reasons do NOT matter – he should be off limits for you if you want a relationship. That is clearly not his desire or agenda. And you can stop asking will he ever ask me out. The answer is definitely no.

Learn how to attract a quality man

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 be something that happens without his trying.

His approach to you is actually quite passive. This might help him avoid feeling guilty. He can say to himself, “I didn’t lead her on because I told her right away I didn’t want a relationship.” Then, when he bumps into you, he’s free to do whatever if you’re open to him.

Passive Men Go Along For The Ride


You say he’s used to pushy women. That’s because he’d rather not be responsible for what happens. This explains why you’re getting the feeling he wants you to pursue him.

The problem is if you pursue him, then you will never really know if he is into you or just going along for the ride. Maybe until something better comes along.

Again, this relates to his passivity. He can then easily absolve himself thinking, “Hey, I told her I didn’t want a relationship but, she pursued me.” That’s why you are SO SMART NOT TOin a  DO IT. Don’t pursue men – it only leads to heartbreak.

He’s Not Emotionally Available

He probably is not an emotionally available man. 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 this?

He is not whole or emotionally healthy. Something is missing or not completely right. He may be a great guy, but that doesn’t mean he’d be a great potential long-term romantic partner.

Attraction is NOT Enough

when will he ask me outI’m not saying he doesn’t like you. I’m sure he does and is attracted or he’d never stick by your side or sleep with you. But you want more than a man who finds you attractive!

You want a man who won’t let you wonder, “Will he ever ask me out?” A man who will ask you out and not leave it all up to chance. The kind of guy who WANTS a relationship that will last and deepen. 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 a relationship with – DESIRE for a relationship. He doesn’t want that or he would do something about it to make you “his.” This is why he bumps into you rather than scheduling dates.

Find out more about why it’s best to let the man lead

Sadly there is absolutely NOTHING you can do to turn this around or change it, He needs to do the healing and he is the only one who can take the needed steps. Often women get sucked into thinking they can help a man heal or change. NO YOU CAN’T. That never works.

Here’s What You Can Do

The best thing you can do is come to grips with the reality of the situation and who he really is. Have the self respect and awareness to recognize a LOST cause.

Instead, rely on your own emotional maturity and skills for self-preservation to do what’s in your own best interest. Let him go and move on. Don’t make yourself available. Don’t stick with him all night.

There are 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.

If you want to learn how to attract a quality man, check out my free audio program.

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.

4 thoughts on “Will He Ever Ask Me Out? Should I Wait Or Ask Him Out?”

  1. I met a guy at my gym. There was flirting in the beginning. I am shy around guys, and he’s shy around me though with others. (He is single). It was just fun to see each other and work out together. But I got tired of this because it wasn’t progressing (i.e., he never asked me out). I withdraw and change my routine, so I didn’t end up seeing him for a couple months. I still feel sparks when I see him, he does double takes when I walk-in. How should I act? Concentrate on working out or try to engage with him a little and some light flirting? I feel like if he wants something with me, it’s up to him at this point to pursue me and ask me.

    • Hi Joan, Seems like you got the point of this post! If you want someone to date, he’s not the one. Flirting is fun, but without action it has no meaning. Since he’s not taken any steps in months to ask you out, he never will. It’s funny – while the gym should be a good place to meet, in my 20 years as a love coach, I’ve not heard of many who fell in love there – except one couple in their 90s! If you are serious about love, try the apps, attend singles events, or check out meetup.com to find groups that appeal. Unfortunately this guy is a waste of your time and heart-space.

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