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

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 outwill 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 y Facebook but didn’t do this before we were intimate.

Pushy Women Take Charge


His last relationship 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.

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.

His approach to you is actually a very passive. This might help him if to 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 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 to 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 great potential long-term romantic partner.

Attraction is NOT Enough

when will he ask me outwhen 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 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.

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. 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.