Question: Why Won’t He Ask Me Out

I like this guy at work – he’s a customer, but there’s no conflict of interest. We interact quite often. From day one, I could tell he was attracted to me. He would give those long gazes but never asked me out. He’s physically bumps into me sometimes, laughs at my jokes, smiles, and of course checking me out from head to toe every time he sees me (even though he thinks I don’t see him). He had recently gotten out of a relationship (moved out) a few months ago. When he found out I was single, he asked a lot of questions about me – education, what I do for fun, who I hang out with. He even was visibly jealous when I was joking around with another guy at work and wouldn’t leave our side. So, over the past couple months, he’s clearly more comfortable with me, and even just in the past couple days, tapping me on the arm and giving me a hard time with jokes. He actually used my cell number (that I gave him for business purposes) to send me a happy birthday text, and after not seeing me for two weeks, he called two days after work for business related stuff. Not to mention the intense head to toe lookdown and gaze he gave me. He clearly missed me, and I gave him a HUGE smile back.

A couple days ago, he mentioned again that he doesn’t have a girlfriend, and that he can’t find anyone. I told him that I found that hard to believe. At the end of the day, I tried spending as much time with him by talking with him and learning as much as I could about him. Over the months, I see how he pumps himself up to me, he managed this amount of people on a base, has significant equity from a previous home sale, pursing higher education, has virtually no boss in his current position, has a pilot license, etc. He’s always pumping himself up in some way.

Anyway, I figure unless he specifically asks me out, I just have to forget about it and move on. But it’s so hard because I’m so crazy about him since knowing him for almost 4 months. It’s hurts so bad…but I don’t want to initiate. A month ago I invited him out with a group of friends and expressed how I’d love for him to come along with us. When I sent him a reminder text a couple days prior to the event, he didn’t respond until the day of the performance with an ambiguous position – if he was around he would come, but he was thinking of visiting a nearby city). I got upset and told him I would just cancel as I didn’t want to hold up his plans, and my friends weren’t able to come anyway. Because of that, I won’t ask him out again.

In that same invitation a month ago, I had also asked him to let me know of any live music coming up prior to that date. It was my way of giving him room to ask me out for any good events. He always talked about what concerts he was going to, and even played video of the most recent performance he went to, and mentioned that he was going to see the guy at a nearby town. But he never invited me. What was the purpose of telling me about all of these events and even playing the video for me on his phone if he wasn’t going to invite me?

The only time we’ve gone out is when he invited me out for lunch at work at an off-site location, and I enjoyed myself, but that’s it so far. As time has progressed, he’s become increasingly more comfortable with me.

I’m so sad because I want to spend time with him, but do you think he likes me, and also, how can I get him out of my mind? He’s the only man I’ve ever felt this way about in my entire 35 years of living, and it’s scary. But I want to also move on with my life…

I can tell he enjoys my company, we laugh together, both are highly inquisitive, driven, and there are so many smiles, stares and “love” pats on the arm or shoulder shared between us. Yet, no date as of yet (after 4 months of working with him). I’m so confused! Please help.


Dan’s Opinion

It looks to me like there is a fair attraction between the two of you, and I can understand your frustration.  Personally, I can’t understand how he isn’t picking up the signals and it isn’t as if you haven’t made an effort to give him opportunities to either go out with you or ask you out.  I wonder if he isn’t just a little ‘gun shy.’  You said he was only out of a relationship a few months back – either there is some unfinished business there or he is unsure how to move forward.  It’s quite possible, if he has been out of the singles scene for a while, that he just doesn’t know what to do next!  I would suggest being up front with him.  Honestly tell him that you have been picking up signals that he is interested, and you feel the same, but you need to know if he intends to do anything about it because you don’t want to hang on waiting forever.  You are both grown-ups, so a straightforward conversation seems the best approach to me!  If he wants to reciprocate, then you are giving him a green light and a confidence boost (because you have taken most of the risk out of the equation) and if he doesn’t feel the same way, you will at least know and be able to move on.


John’s Opinion


There’s almost no doubt in my mind that this man is into you and there’s clearly a significant amount of chemistry between the two of you. That said, his actions, or lack thereof, point to a personal issue. He’s being cautious.

From what I gather, you have given him every opening and opportunity to ask you out. You’ve actually made it quite easy, it couldn’t be easier. The fact that you described him as driven and a man with a long list of accomplishments, (or perhaps he’s described himself in that way) it does mean that he’s not one to get cold feet. When he wants something, he finds a way to get it.

You said he recently ended a relationship, one in which he lived with his partner. He sounds like a man who experienced the type of break-up that you only want to go through once. Meaning, before he starts something serious again, he’s going to make sure he’s both ready and that the woman is the right one for him. Once bitten, twice shy. Perhaps he just doesn’t want to rush anything before he’s ready.

It’s much easier for men to start something with a woman with whom they know it’s not going anywhere with, then to start something with a woman that they can see a future with. The latter must be done properly, with a clear mind and whole heart. If you’re the type of woman he can see a future with, the last thing he’s going to do is rush into it. But he’ll give you enough to keep you interested and to let you know he’s fond of you, just not ready yet.

My advice, be patient and continue to build the relationship but watch for signs of his affection for you wavering. If it begins to waver, don’t hang on too tight, let him go. If it doesn’t and things continue to progress as they have been over the past four months, then hang in there. Progress is progress. It doesn’t hurt to tell him how you feel about him, though, I highly doubt he already doesn’t know. But you’ve waited this long, and yes, it may feel like your life is on hold, but isn’t someone who you are compatible with worth waiting for?

Build the relationship and have fun with it. If and when you do finally get together, you’ll have laid the groundwork down for a solid relationship and you’ll have a partner that is not only your lover but your friend.


Paul’s Opinion

There are two big factors that I believe are messing this courtship up.

1) He just got out of a relationship where he was living with his ex-girlfriend.  That is never an easy breakup and always emotionally draining. The last thing he probably wants to do right now is jump back into another serious relationship.  If he sees you as someone he can become serious with, he will definitely take things slowly.

2) With the last bit of information on hand remember, he frequents your place of work.  If he does decide to go ahead and start dating you and things go bad, (probably because he wasn’t ready to start dating) he now has to deal with you being upset with him and the awkward situation that will develop every time he sees you at work.  Not only does this hurt you, its going to make his life much more complicated which he doesn’t need since he is trying to straighten his life out after his last break up.

So what exactly is he doing?  He is being cautious, he is making sure he doesn’t jump into another relationship head first.  Instead, he is trying to learn as much about you as possible, from a safe distance.  That way he can determine what kind of a person you really are before he does decide to ask you out. He doesn’t want to end up in the same kind of relationship he just got out of.

One other thing I want to point out, while I know this situation can be awkward to deal with when you are at work.  I do commend you for asking him out to the concert, that was a safe move.  However, how would you feel if a guy asked you out by inviting you out with a bunch of his friends.  There is nothing worst then being the fifth wheel out with a group of really close friends.

Also I know rejection can hurt, especially when you really like someone, but only giving him one chance when technically you never really asked him out is a little hard.  Since you guys both like going to concerts, find a concert that is playing three nights minimum.  Next time he comes into work, tell him you really want to go see this band (make sure he likes the band too) but none of your friends want to go and you can’t go alone. Then all of a sudden you realize that he likes that band, so why don’t the both of you go together. Let him know the band plays for three nights and pick the best night that works for the both of you.

Now he has no excuses.  You are going to go see a band he likes, no friends, just the two of you for a fun night.  If he says no to that, then its time to move on. However, if you are only going to drop hints as to ways he can ask you out, or play things safe by inviting him out with your friends, then you will have to be patient.

One thought on “Question: Why Won’t He Ask Me Out

  1. robert
    October 10, 2012 at 9:21 pm

    I could be that guy. A woman with whom you see the possibility of a future is scary after being in a relationship. You want to be sure that you are not making another relationship mistake and just observe and learn. I know I have wanted to ask the woman out many times over many months and yet waited. I even set a 90 day rule where I decided to wait 90 days before asking her out to make sure I felt the same. At the same time I still chatted her up and visited her office 2x a week and gave her t small gifts and flirted . She became titillated and frustrated with me. Be direct and ask him to talk with you at a happy hour bar nearby where you both arrive separately, talk about your attraction and listen.

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