He Flirts with Me, So Why Doesn’t He Ask Me Out?

Why doesn't he ask me out
Why doesn’t he ask me out

If you are wondering why, “He flirts with me but doesn’t ask me out?” read on to finally learn what that is really about.

Has this happened to you?

There’s a guy at work, church, or in your social circle. When you see him, he seems to light up. He seems very interested in what’s going on with you and catching up. He may flirt with his eyes, or verbally, or even touch you lightly. For some women, the man has actually taken things as far as kissing you once or twice.

Every time you see him, you experience the intense excitement of attraction. You feel prettier after talking with him. Your heart might be going pitter-patter. Its such a great feeling, exhilarating really. He must feel it too! How could you be the only one feeling this? There’s absolutely no way he doesn’t feel this same electricity. The same attraction. The same excitement.

But, and this is a huge but, you still don’t know –

Why Doesn’t He Ask Me Out?

Your relationship is stuck at flirting. And it drives you completely crazy. You simply cannot stop thinking about him.

Every time you run into him (which might be daily, once a week at church, or occasionally in your social circle), afterwards you spend days going over every detail of your interaction. What he said. His smile. The way he looked at you. How he lightly touched you on the arm or shoulder and the sensations that coursed through your body as a result.

Which leads you to wonder, “Why doesn’t ask me out?” This question creates a certain degree of frustration because you do not understand!  He’s ending mixed signals. How can this be? Why doesn’t he take it to the next obvious step?

I have had several dating coaching clients tell me about these interactions at church, the gym and at work. Other people have asked you about the situation, thinking you must be seeing each other. They’ve noticed how things are between you. How can they see it, but he doesn’t do one thing about it?

3 Reasons Why He’s Not Asking You Out:

1. Oh yeah, he’s attracted to you.  However, he is actually involved with someone else. And for whatever reason he doesn’t want to mention that because he enjoys flirting with you. It makes him feel good too. It’s really fun and good for his ego. Attraction isn’t enough when it comes to finding a compatible partner.

2. He isn’t ready or looking for a relationship. But flirting with you gives him his “feminine fix” and then he’s on his merry way. He definitely benefits from flirting with you. It makes him feel alive and wanted. He loves the attention you give him.  Yet, he has no intention of ever taking this one step further and he’s probably not emotionally available.

3. Something is keeping him from being active romantically. It could be financial trouble, health issues, emotional baggage, a horrible divorce, or any number of other concerns. It doesn’t really matter though because he’s not moving forward any time soon. A man who doesn’t have his life together has little room for love.

Why is this so confusing and agitating for you? Here’s the answer in a nutshell –

You mistake his flirtations and interactions as being in some sort of relationship.

A relationship with potential or promise. That’s a huge perception problem for you. The truth is, THIS IS NOT A RELATIONSHIP! And sadly, 99.9% of the time, it never will be. This is a clear cut case of a man sending you mixed signals – he’s attracted and pays attention to you, but he’s unwilling to take things any further.

Does this mean flirting with this man is a waste of time? Not necessarily. There are some benefits as long as you are clear this is going no where. Flirting like this:

  • Builds your flirting and conversation skills
  • Improves your confidence and self-esteem
  • Makes you feel more attractive and desirable
  • Allows other men to see how great you are in action
  • Can be a great love life launching pad, if you allow yourself to not get lost in it

This is the biggest problem with Mr. Flirtypants:

He Is Not Mr. Right. If He Were Mr. Right, He’d Be Asking You Out.

He has some major flaw that keeps him from entering a relationship with you. Please don’t forget that essential piece of the puzzle to remind yourself he’s not the one. The right man would never leave you asking, “Why doesn’t he ask me out?” He’d ask you out and spend time with you!

If you find yourself in this situation, evaluate how long this has been going on and if there is any reason to believe, in reality, if he’ll ever ask you out. Remember, 99.9% of the time, nothing will ever happen and these are dead end situations that disappoint you and take you away from your mission – finding love.

PS – Get help with understanding men in my free book His Mixed Signals Are So ConfusingSave




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.

183 thoughts on “He Flirts with Me, So Why Doesn’t He Ask Me Out?”

  1. Hi Ronnie, I’m the lady from a few posts ago. Since the post, the guy’s asked me out two more times and I keep saying no. I’m going to a fence shop so that I can build higher boundaries! Sorry about screwing up your topic.

    Wanted to say thank you for taking the time to reply and giving me sound advice.

  2. Hi Ronnie,
    I am currently in this type of situation. For about 3 months a guy at work and I have been flirting. It started with him telling me how pretty I was. He continues to compliment me all the time tells me I look good hugs me and hangs around when I’m there . In the Beginning I had got his number from a friend because I did feel he was interested and asked him on a date he politely said he had other commitments and couldn’t go although he would have loved to and next time just let him know in advance. He did not offer another time to get together. Since then I have not asked him out again. He continues to flirt and still acts interested. He never texts me first but always responds very quickly when I text him they are flirty texts nothing sexual although the he did say I’m his weakness. Lately he had been asking more personal questions about like what I do when I’m off and asks me if Ive gone to anymore of the events that I 1st asked him to go to. I’m confused if this is just a waste of my time.

    • Hi Jana, Don’t be confused. As I said in the post, if he wanted to date you , he’d ask. At least he would have said when YOU asked. But he declined. If you like flirting with him, then enjoy it but stop expecting anything to come from it. This is a huge dead end. The biggest clue is in your own words, he “acts interested”. Men who are interested don’t “act” they ask and go out with you. Move on – this guy is seriously wasting your time.

  3. Hi Ronnie,
    Thank you so much for this article. I seem to be stuck in a loop of “always the friend, never the girlfriend” I just recently moved to a new city and started a job two weeks ago. A male coworker of mine is flirty with all the other ladies during the day (but not with me) and after hours (I work a little later) he flirts with me and we have light banter. I know I’m not his type; the ladies said he prefers Asian women (and I am not). Though the other night after work he gave me a book to read he thought I’d like and that surprised me. I think he’s just being nice and I don’t want to get caught in the loop again. I’m a few years older than him (though he thinks I’m the same age as him; he presumed) he won’t believe me that I’m older; though I never revealed my actual age. I think that perhaps I’m lonely and we both enjoy the flirtation?

    • HI Alice, your guess could be right. He simply enjoys flirting and its fun for you too. The trouble comes when you think there’s more to it. To stay out of the “loop,” don’t attach meaning to a man’s flirting. Another way to keep out of the circle as you put it is to do something to meet new men. You might be getting stuck on the guy who hangs around. Instead, do something to meet men so you can find one who wants a relationship.

  4. Good for you Deb! You are so right – you don’t need friendship like this with a man like this. It would absolutely suck you into his drama.

  5. Ronnie, thank goodness you replied back…I’m glad I had the sense to say no….I guess I thought I could be a friend by listening, but that just sucks me into his drama! Deb

  6. A guy at work has always made a point of coming down to see me every now again for conversation, but lately, he’s been coming by once a week on a regular basis. We bumped into each other by accident one day and there was this warmth and instant attraction. I was floored! Here’s the kicker, he came by to tell me about a girlfriend problem and wanted my advice (he never mentioned anything before, and I never asked). Leaves my office and sends me an email to go out for dinner. I reply with a huh? He then tells me that he would like to talk some more and for me to meet his girlfriend. I declined gently. I’m confused – I think I blew it on the dinner, but didn’t want to meet the girlfriend knowing that I was developing feelings for the guy. So why didn’t he just ask me out when he was in my office? Now he’s all serious, I’m still friendly. It’s awkward. Is he shy and testing the waters?he has shown some romantic interest (when he thinks I’m not looking). I guess it’s time to start dating more men….this is taking up way too much time! Deb 🙂

    • Hi Deb, Are you saying you want to meet a man who has a girlfriend already? Who needs him if he’s planning on cheating with you? Is he testing you? No and I don’t recommend dating any man who would “test you”. That’s not sincere love interest to behave that way. Shy? How could a man be shy who asks you out to dinner to meet his girlfriend? That’s not shy – it’s strange and ballsy. Or perhaps he is attracted and hopes his girlfriend will like you too for a three-some. None of this gives me hope for honest, monogamous, lasting love.

      The one thing I’m in complete agreement with is that you should definitely date other men. In addition, I hope you think about your value as a human being and a woman so that you build confidence and learn to draw strong boundaries. This way, you won’t date men who tell you they plan to cheat or have other odd arrangements in mind. You deserve to be treated with respect. Please remember that.

  7. I met this guy on the train. He pursued me. We see each other occasionally on the train and chat about work, life Etc. Then he asked me to lunch. I gave him my card with my cell #. He called me and we went to lunch. After lunch he hugged me and gave me his card with cell #. He said I’ll see you on the train. Did not see him for a few days then saw him and talked today. The talking seems to be getting more personal. Then he said he was going to take me to lunch again.

    He does not wear a ring. He came up to me and introduced himself first. He took me to lunch and paid. I never asked if he was married the time has never been appropriate. He has never text or calked me. I’m confused as to what we are. Friends? Is there something going on in his life? He talked about his kids but never about a wife just his buddy’s. He is a gentleman and a very nice guy and I know people who know him and say he is not a cheater. What is his deal? Can I ask if he is married because I do not want to be going to lunch with someone’s husband.

    • Hi DeAnna,
      He may not want a relationship but enjoys talking to you and wanted a bit more with lunch. or he might be curious about you but super cautious. If you want to casually ask him if he’s married, go ahead. You could say, “You’re not married or in a relationship with someone are you?” Then see how he responds. If he looks away, that’s not a good sign. In the mean time, this is the perfect place to start dating other men so you don’t over-focus on this one man. xoxo, Ronnie

  8. thanks for your posts Ronnie. I’ve learnt quite a lot from them. I am in a similar situation right now. There is this very shy guy in my church who gets very uneasy and nervous around me and looks away whenever our eyes meet.
    He seemed to have confided in his friend that he has feelings for me because he (his friend) is always doing things to bring us together. Recently he’s been making efforts to be friendly and I have done all I could to make things easy for him because I like him a lot.
    He still hasn’t asked me out. It’s been over year. is he ever going to ask me out? Should I give up on him?

    • Hi Tobby, I hate to say it but after a year if he hasn’t mustered up the courage yet, not sure he ever will. Yes, I agree – move on. If he has a hard time with just eye contact, he’s not an emotionally available man.

  9. Ronnie,

    Thanks for your quick response!

    I thought intense sexual chemistry WAS love. I guess I did doubt his sincerity (well founded, as it turned out) And I am terrified of opening my heart and being hurt. Unfortunately, this has validated my fear. The part that makes me feel so bad is it was like it never happened, but I know it did! Maybe he saw something in me he did not like–or realized I really am to old for him. I look great for my age, but you can’t fool Mother Nature.

    If the intense flirting (I looked into his searching eyes and was captured and lost all sense of reality/time and had to really grab myself in order to maintain my composure) I was certain something would happen. Enough so that I was really preparing myself for it. So the shock was, well, shocking.

    I wish I had just left it at the professional question and not continued with my apology. He seemed to not have a clue anything had happened at all. Odd that he called around five Saturday evening, it would have been the perfect opportunity to ask me out and he obviously did not want to!…….But at least I know now.

    No one knows how strong my feelings were, (except my hairdresser!) and I don’t think I made too much of a fool out of myself so I should be able to recover pretty unscathed. I have decided to resign my post on the Board of Directors and minimize any further contact. It’s not the only reason for resigning, but it is definitely the clincher.

    A therapist would not help. I know why I reacted like that, and that reason is not going to go away–ever, I’m afraid.

    Thanks for your thoughts. I appreciate knowing how common this sort of thing is. I enjoyed reading the thread. (misery loves company!)

  10. I have recently found myself in a not-so-nice situation with a man I do volunteer work for. I had interacted with him during some pretty intense physical work. I always ignored him, thinking he was way too young and was no doubt married or had a girlfriend. I never even looked at him. But then he started coming on real strong to me every time I saw him, The eye contact was intense. He looked so deeply into my eyes–searchingly, like he was trying desperately to communicate with me. He flirted shamelessly with me in front of everyone.

    I was so taken aback by this. I was like “what the hell!” but then I really let myself fall for him. I was so scared by how i was feeling it totally freaked me out. So I gave him very negative feedback of ignoring him again and I felt this one day I had really been unfriendly to him and felt badly for it because that is the opposite to what I was feeling.

    So I called him about a work related question. He didn’t call me back right away–he’s a busy man. That was a Friday. Then he called me back on a Saturday around five. I asked the work question and told him I was sorry for being unfriendly at the meeting. He said he didn’t notice anything and he could guarantee me he would not have noticed anything about me. anyway. Nice. Ouch!

    It was so intense the way he was coming on to me I was absolutely floored by this. I feel like such an idiot. After those looks and his falling all over himself around me! I truly give up on love.

    • Barbara,

      Before you give up on love, please think about this – was this love or was it intense sexual chemistry? If this guy was so intense but you went for it, that’s one thing. The next area to look at is how you treated him in response because of your own fear. Is that love to you? This situation has a lot of learning that can come from it. Don’t give up now. Spend some time to unravel what happened.

      Be honest with yourself. Were you cold because you are afraid of love or because you doubted his sincerity? You may even want to work this through with a therapist just for objective feedback. Understanding your resistance and reaction will tell you a lot about yourself and could really free you up to find the love you want that wasn’t available with this man.

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