Is He Shy or Not Interested: How Can Women Move First?

Is he shy or not interested? How do I give him the benefit of the doubt? Am I missing out on a great but shy guy? Am I judging him too fast on a dating app? Do I need to wait to meet him in order to gauge his interest better? Does he need more time in order to get more comfortable with me? If yes, how long do I give him a chance to get comfortable in getting to know me? And when to know exactly if it is time for me to stop putting in effort and move on to the next guy?

Well, I am pretty sure that if you have ever encountered a shy guy in your life when dating, you would feel unsure if you should give up or you should give it a little time for him to open up to you and catch up with you at the pace you are moving on with your dating life.

Giving the wrong person a chance can be hurtful, but passing on a great but shy guy can be even more painful especially when you come to know that you have hastily looked past his great qualities just because he took a little bit more time to open up and talk to you.

We all would want to avoid judging people too fast (I’m sure you have struggled to understand the signs he is waiting for you to make the first move) but at the same time would also want to save ourselves the time we invest in people so that we don’t get stuck with a date that is not moving anywhere further. And striking a balance between the both is what we always struggle with.

A man wearing formal attire and a woman wearing white dress walking along the street, as the woman pushes his hand, trying to find out if he is shy or not interested

As someone who has been in the dating scene even before my 30s, and stretching through my early and soon mid-30s, I am here to share my thoughts (actually speaking my thoughts as I am so excited to have found the speech-to-text dictation Google Chrome extension that saves me 66% percent of my time typing – oh, and it is FREE, takes 5 seconds to install and only up to 10 MB of your computer memory! How cool!) on how I work through my emotions and what has worked for me in facing this situation, so that you can navigate through this phase gracefully and teach your mind to discern make better decisions in dating.

Share this post around if you find it useful or interesting!

Affiliate Link Disclosure
Some of the links in this article may be affiliate links and I may earn a commission if you click on them, at no additional cost to you. Hope you find the information here useful! Thanks. 

Is He Shy or Not Interested?

Finding out if he’s shy or not interested or have the love intention can be a challenging task, especially for women, when we are always expecting men to make the first move. Women also find it difficult to make the first move as they fear being judged by men for approaching them first. It has all been ingrained in the society and the way we were brought up since we were young. This is expecially true as women don’t want to end up in discreet dates and be careful so that they don’t fall in love with potential.

However, if you would like to know if a man is just shy or not interested, you as the woman, should somehow make the first move. But what women should understand when approaching a shy guy are the following aspects:

  • Women should know when to stop putting in too much effort
  • Women should feel confident and carefree when approaching a guy who is shy
  • Women should understand that making the first move is not so much about gender roles but about expressing our desires and putting in the effort to make the desires met
  • Women should know how to make a guy comfortable in order to open up and speak to them
  • Women should understand that efforts should be mutual and initiatives must be reciprocated along the way.

How To Know If Approaching a Shy Guy Is Not For You?

If you’re reluctant to make the first move, approaching a shy guy will always feel strainful to your mental health as you will always feel like giving up on your self-esteem and respect in order to approach the guy first.

If you’re constantly worrying that you might be strung along by men who have avoidant attachment dating style when you approach them first or if you do not know if they are interested in you or not (even after reading this post and all the other advice given by dating guru), you should reconsider the option of approaching men first in order to save your sanity.

How To Know If He Is Shy But Interested?

A shy guy who is interested in you will show signs that he is interested in getting to know you but is taking some time to get comfortable in talking to you. Here are the following signs to potentially look for but this is a non-exhaustive list. So, keep in mind that you should be looking out for other signs and always listen to your intuition to see if the guy that you’re talking to is indeed interested in uh bridging the gap between the both of you.

  • He tries to reciprocate conversations and messages you although the messages can be cringy or awkward at times.
  • You can literally feel him getting shy or uncomfortable when talking about things that can be a little bit uncomfortable for him like past relationships and his preferences in romance.
  • You do not necessarily need to be the only one initiating conversations like text messages especially.
  • Shy guys have a problem asking you out or even giving you a phone call because they fear that you would be feeling disturbed by their effort, but they would make time to meet you when you initiate meet-ups.
  • They would get comfortable with you as time goes by and catch up with your face in dating and meet you halfway.

What To Do If He Is Shy, Seemingly Interested But Reluctant?

You may feel that he is seemingly interested but he is shy and also reluctant at the same time if his words do not match his actions. He may tell you that he is interested in getting to know you and that he is invested in looking for a partner for a long-term relationship, but he hardly initiates conversations to get to know you, and he does not plan for a meet-up.

This is where you may think that he is seemingly interested but you would also be quite puzzled by his reluctance at this point in time and you may think that he is actually a shy person. There is no harm in actually giving people the benefit of the doubt, especially when you think that you like them and you would like to see how far this can go.

In this case, you would need to set the timeline realistically for you to see if the person is catching up with you and reciprocating interest. You would need to be very mindful and see if they are improving in terms of communication intensity after you initiate conversation say about five times.

The number of initiatives taken is totally up to you and you can even decide to see if they are getting better after say about two days that you will have initiated on your own.

If they are not reciprocating still, do this instead:

“Hey, I really think that you’re a nice person and I feel that I would like to get to know you a little bit more. I do feel that you are shy and probably you would need a little bit more time to get comfortable in opening up and talking to me. Hence, I have tried to initiate conversations with you in the past and also planned for dates. However, I think efforts should be mutual and I feel that at this point in time, I would like you to reciprocate my effort so that I know we are on the same page. If not I think it is good to put an end to our get-to-know sessions so that we both can find somebody who is more suitable for us.”

If he is interested in you would feel the pressure and communicate with you about how we feel in order to not lose you. If he does not do anything about it, it could mean that he is actually not ready to have a relationship with anyone and probably he has not done enough inner work in order to step up and talk to people.

In this case, it is actually not your responsibility to fix somebody who is emotionally unavailable. He could be the nicest guy that you can ever find but if somebody is not making the effort to talk to you, things are not going to go far.

How To Know If He’s Actually Not Interested?

You may ask, “if he’s actually not interested, wouldn’t you know that instantly? You wouldn’t even need to be confused if he’s actually shy or not interested”

I hear you! We always get confused about people especially when it comes to reading their words and also trying to match if the words reflect their actions. If somebody is actually not shy but also not interested, they would probably tell you then and there that they are not interested in getting to know you and you would have gotten your closure immediately. However, we get confused in knwoing if the person is shy or not interested if there is no direct rejection provided.

Natalie Lue whom I admire a lot for her work sheds light on why did he respond if he is not interested in me?

This is where initially we would feel like giving them a chance in order to really understand if they are actually shy so that we do not miss out on a great guy. However, below are the situations to pay attention to in order to identify if somebody is actually not interested whether or not he is a shy guy.

  • He does not initiate any texts. Shy guys tend to feel more confident behind the screen as compared to face-to-face communication. So, if you are still not getting any text messages from them especially text messages that are initiated by them, they are probably not interested in you.
  • They are not comfortable around you and this uncomfortable feeling is rather a sign of displeasure which should not be confused with signs of someone being shy.
  • If they do not want to make plans to meet you, it is a sign that they are not very much interested in getting to know you.
  • Things do not improve as time goes by. Even after giving a full month of time for him to get comfortable talking to you after you’ve initiated conversations if he is not getting closer to you and the intensity of the conversation is not escalating by now, he’s not interested in getting to know you.

How Long Do I Wait Until Its Time To Move On?

How long to give for shy men to feel comfortable talking to you is something very subjective and it may differ from one woman to another. In the context of women above 30 years old, who probably do not have a lot of time to waste on men who are not intentional when it comes to dating, you may give a man a maximum of a month in order to see if there are any improvements in getting to know you.

You should also see if they are responding to your initiatives after a couple of times of initiation. They should be giving you some level of signal that they are feeling better when talking to you.

Give them the chance to miss you by not sending them text messages or calling them over the phone abruptly for a couple of days and see if they text you. Go about your life and do not stress if they would circle around.

How To Make Him Comfortable In Talking To Us?

There are a few things that can be done in order to make a shy guy comfortable in talking to us:

  1. Do not talk about things related to relationship and romance directly. Instead, invite him to watch a movie with you virtually where the both of you can be at the comfort of your own homes and still watch a movie together from your own devices. I have done this exactly the past and I feel that this worked really well in order to break the ice between two people. Pick movies that are related to romance and then later on ask the guy what he feels about the movie.
  1. Initiate the phone conversations first. It does not really matter if they are busy. Do ask them that you would like to talk to them and see how they react to it. If a guy is really interested by shy to talk to you, he would snatch the opportunity to talk to you.
  1. Send them your lunch photos and random activities that you are doing in order to create a space that is warm and welcoming for them to share tiny bits of the lives with you.
  2. Initiate a video call conversation with them in order to really get them comfortable in talking to you face to face. This would be a great activity to do before you guys meet in person as by then they would feel more calm and composed and the date would go pretty well.


How to tell if a shy guy is interested in you or just being friendly?

  1. he would like to go to on a date with you and prefers to exclude friends
  2. He will be consistent in communicating with you, like asking if you have had your dinner and what you are doing at the moment – things that normal friends would not really do for a friend.

3. He will talk about relationships and try to understand your preferences in relationship.

A guy who is just being friendly would not overly be interested on your relationship status.

How can you tell the difference between shy and uninterested?

If they are shy but interested, they would blush when being around you. They would not necessarily avoid you and would like to be around you. If you find them getting attracted to you and trying to find excuses in order to see you, then they are interested in you but are being shy. Even a shy person will glance and make eye contact, if it’s only brief. But if they intentionally avoid it – they’re not interested.

Is he nervous around me or just not interested?

If he’s generally a pretty nervous guy, him being nervous around you may just be his normal behavior. However, a nervous guy that is not romantically interested in you would feel comfortable after a few times talking to you. If he is still being nervous around you even after getting to know you well, it could be a sign that he is interested in you romantically and therefore getting nervous when he is being around you.

Is a shy guy interested?

A shy guy is interested if he likes being around you, sending you gifts, smiling at you, or sharing his secrets with you. You can find him sneaking his way to strike the conversation with you which usually can be very awkward and cringy. It can be a little bit difficult to identify if a shy guys interested because they can’t be very good at masking their feelings and therefore their intentions can be hard to identify by women.

Scroll to Top