Should she make the first move with this introvert?


Here’s a question from someone who would really like to date an introvert and wants to know if she should make a move – or if that will run him off forever!

Hi, I really like my introverted boss and am not sure how to let him know without scaring him away forever. I did get a fit of nerves for fear that I would never tell him how I felt and asked him if he would ever let me into “(insert fake name here)ville” as that is what he calls his inner world and he replied probably not. I don’t know if that’s because I asked him at the end of a night full of socializing including being at a noisy nightclub with a bunch of people, or if he really just doesn’t want me invading his walls with my borderline introvert/extrovert chaos.

I have a lot of introverted and extroverted tendencies, but I am intelligent and very good at what I do. This man is so unique that I spend a good deal of time defending him to the other people that we are currently away on course with. I like him because of his uniqueness such as his sense of humor, which not many other people understand as I think they are not smart enough to get it, the fact that he doesn’t need to be staring at hot women to affirm his manliness and the conversations we have together when we are alone are the most intellectually stimulating and challenging talks I’ve had with anyone for a long time.

He protects his private time ferociously which I understand, and occasionally will take the “Do not Disturb” off his door which I think means that he wouldn’t mind too much if I visited. His body language strongly suggests that he likes me, he often stands close to me, and will quickly glance at me when he thinks I don’t know. Am I crazy to think that I could have a future with someone as special as he is or should I let go of the heart ache now before I fall too deeply for him.

Photo credit: Nina Matthews Photography



  1. Go for it! If like you say he is very introverted then the chances are he is not going to make the first move. Also you said you’ve noticed him glancing at you and often stands in close proximity, which for a shy person may be the only signals of interest you will get. Either way if you don’t try you will regret it much more when you look back than if you go for it and he says no.

  2. If you’re having long, deep conversations with an introvert, then he IS letting you into his inner world. Conversations in general require energy for us, so we don’t go around having extended, complex discussions with just anyone.

    If he’s introverted and shy (not the same thing, but often found together), and he hasn’t had a lot of success with women (par for the course, unfortunately), then you may have to be very blunt. He’s probably oblivious to the body language cues that you think are clear signs, like standing extra close. Give up subtlety. In those conversations, he’s surely mentioned some things he likes to do. If he’s into art, find an exhibition that’s coming up and ask him to go with you.

    Since he’s your boss, that could also be holding him back. If he asks you out — no matter how carefully — and you aren’t interested, that can be very dangerous for him in today’s climate. So you’re going to have to be even more blunt and take the lead more than you’d probably like, to make it clear — even to a man — that you’re interested.
    Aaron B.´s last post ..Our Mother of Perpetual Help

  3. He’s your boss? Then no, don’t ask him out.

    Someday he won’t be your boss, at which time, yes. But until then, no.

  4. I think Aaron B. had some good advice. The only thing I would add is that, as a shy introvert myself, being forceful is never a good idea. Even if “no” is the last thing I want to say, I don’t want to feel like I’ll be challenged if that does happen to be my answer. People who push too hard and too fast typically make me shut down faster than anything, so keep that in mind. But otherwise, I’d say go for it. Don’t ask him for a relationship at first, just ask him for a date- for a chance at a relationship- and see how it goes.

  5. Do you know how he is with written communication? Perhaps, if you do choose to go ahead and ask him, he might feel more comfortable with the question/invitation in writing. Since part of the hallmark of introversion is a slower reaction time, it’s often difficult for us to respond to unexpected things quickly and intelligently, even when we are quite quick and intelligent. I prefer all important discussions to be opened up in writing so I have time to process them before being forced to talk about them. Talking is difficult, when it’s something that touches me nearly. I want to instantly reject emotional matters when they’re just sprung on me and I have to respond to them immediately.

  6. The bad part if he isn’t feeling the same way. You must make sure he’s into to you by giving angles and signs but never make the first move. He might think you’re easy or something. Being a man is different to being an introvert 🙂

  7. Thank you all for your advice. I have decided to back off until he is no longer my boss. He is a man in a million and I don’t want to scare him away. I think contacting him through writing is the perfect way to go as he has always responded positively to any form of written communication I have with him. I appreciate your time

  8. He’s probably oblivious to the body language cues that you think are clear signs, like standing extra close. Give up subtlety. In those conversations, he’s surely mentioned some things he likes to do. If he’s into art, find an exhibition that’s coming up and ask him to go with you.
    Carla´s last post ..Dealing With My Own Frustrations

  9. At first I thought this was a joke but I guess some people are taking it seriously so I will try to do the same. My advice:
    1) He’s your boss! No, don’t touch that thought with a 10-foot pole! Are you nuts?
    2) He puts that “Do Not Disturb” sign on his door for a reason. It is rude to remove it.
    3) Find a co-worker or someone else to have a fling with.

  10. I think that woman should never take the first step, even a man is an introvert. This is not correct, the man must always make the first thing to do a replacement relationship. He must take the initiative

    • Look at you!!! No way man will make a first move. Man and Women are equal humans. Especially with introverts. Introverts wont even make the move. If you dont like it I suggest dating a another women or bad boys. Also its 2012 not 1950. Today most ppl cheat others or leave them this make it less likely for man to make a move again. That word cheating are much more sensitive for introverts because they hate getting hurt and dont have the useless energy like useless bad ppl that can deal with it. They believe in one thing. One man One women hookup and living forever together. Do we get this of today? NO!!

  11. See as you have written above that he is an introvert he is definitely not going to make the first move, you have to do it. If you feel that he likes you then ask him out, because the chances of him asking you out are very slim. And moreover he wont give you many signals, so just go for it.

    • Its also not easy for introvert guys to make a move. Girl or boy it does not matter both are equal nothing more. If one have feelings for other they must make the move especially if it comes to introverts

  12. i had asked a question some time back but i couldn’t find that post over here, neither did i get any reply. can anyone tell me why

  13. “The bad part if he isn’t feeling the same way.” This statement is the “ouch” part!
    Anyway, for me I’d prefer if the woman does not make the first move. Although I feel for you. It’s hard to be loving in silence. There’s that increasing feeling that you need to burst out how you truly feel for him. I can relate to it. Anyway, just take you time. Develop your friendship with him as a person and as your boss.

    • No its not hard for women to make a move. Dont come up with excuses. With any introvert women should make the move end of story! Interest = move is all women can do but make it very very obvious women are interested

  14. Well that is really sweet. I mean go for it. But you have to take it slowly because you might really scare him off because knowing he is you said introverted. it would be a challenge and as time goes by if he really likes you he will have the guts to tell you that is if you don’t give him intimidation that other girls do to guys.

  15. By all means go for it. An introvert will normally not make the first move and much less in a work environment. If you just wait, you’ll be waiting for a long time.

    Just remember the old wisdom about relationships at work. If it doesn’t work out at the end, you’ll still have to see this guy every day, so weigh your options carefully.

  16. Yeah that’s right try to back off a little bit until you decided not to become her employee. Regarding communication as you have said he replies very positively in written form if you really want to ask him out then a one on one personal conversation is only the option to know and get some answers.

  17. yes… do make the first move… but at the right time. i am a male, and an introvert. i always find it very sweet when a girl makes the first move.

  18. Your situation is a bit more complex due to your work relationship. The work environment can already be stressful and uncomfortable at times, and you risk making it harder on yourself if things don’t go as planned, after all, he is your boss.

    Speaking from experience as a male introvert, I regret not telling the woman I cared about for years my true feelings. All I did was analyze her as if trying to solve a mathematical equation in order to figure out if she was interested. I wish she had made the first move, because as much as I wanted to, I could not bring myself to do it. This would not have scared me away nor would I have taken her for granted. It would have been a relief for me and actually of great help.

    Weigh your options if it’s going to make you feel any more comfortable; What can you live with? What can you live without?

    I recommend ultimately going with your initial gut feeling.

    – Good Luck!

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