Dating a Shy Guy – How to Make it Work

There is sometimes nothing as confusing as dating a shy guy. From when the first date gets mentioned to the introducing-him-to-the-friends stage, it can always be a little difficult to work out where you stand.

guy thinking worried

Does he fancy me but is being slightly off with his messaging because he’s shy or is it really because he has just gone off me full stop? And then there is the broaching of sensitive, awkward subjects that are made all the more difficult because you know he gets uncomfortable. So, here’s a useful guide at how to make dating that little bit easier when he is a shy guy.


This can almost be the worst part because you must take matters into your own hands if you like him. It can be a brave step because you do not know if he is just shy or merely not interested so having the courage to make the first move is admirable.

1. Communicate over social media

Get in touch on social media or even just messaging. However social media allows you to message someone without having to have the conversation asking for the phone number beforehand. By talking to him over an account first allows you to feel more confident in testing the waters and seeing where he stands while also enabling him to feel like he can open up more without being so exposed.

People are braver when communicating by these means and it can help you establish whether or not there is the potential for something to work here.

2. Take things slow ­

It’s not always true but if he’s shy, he may also scare easily. Therefore, rather than being overly open and fast paced right off the bat, take your time so you can build up a solid conversation before suggesting going out for a drink.

This will make you both feel more comfortable in each other’s company and take the pressure off a little bit when you finally go on your first date.

Also read: Best dating websites

3. Compliment

Be sincere. Shyness usually comes from a place of insecurity and lack of confidence; therefore, be sure to give honest, genuine compliments that will raise his self-esteem.


Now that you’ve opened up some form of communication and the first date has been set, be sure to be just as attentive and responsive to make him feel as comfortable as possible.

1. Confirm

Regardless of who suggests the date or not, if it’s a few days away then people can always be a little nervous that it’s not actually happening. Therefore, just to remove one stress from the situation, be sure to communicate with him right up until the first day so that you both are certain it’s occurring.

2. Ask and talk

It’s important to ask questions about him but know that the talking will fall primarily to you, or at least in the first few instances. One of the greatest worries people have about dating is that there will be nothing to talk about and this is only accentuated when you are shy.

Thus, while you want to show you are interested in them and ask questions to find out more, don’t be fazed when their answers are brief and you are having to be responsible to hold the majority of the conversation.

3. Keep the topics light

If someone is shy, it takes them a little longer to be overly open about themselves. Don’t ask too many personal questions all at once as this can make them feel uncomfortable.

Also read: 3 Mistakes men make in relationships

Meeting the friends and family

This can be a stressful and big moment for any individual and this can be made all the worse when you are shy.

1. Firstly, don’t rush this meeting

Throwing someone in the deep end too early can rock their confidence and make them nervous for meeting anyone close to you.

2. Play it down

When you make something seem like a huge deal, you feel more nervous. Thus, by emphasizing how chilled it will be can help ease nerves.

3. Drip feed

First introduce to the sibling. Then maybe the friend. Then maybe the sibling’s partner. Thus, when it comes to dinner at the parents’ house, your boyfriend can feel more comfortable because he already has formed friendships with other people present.

4. Tell them how much they were liked

While your family will probably all say lovely remarks about your partner, do be sure to pass these on. Nothing will build their confidence like hearing comments like that.


Most importantly, when dating a shy guy just know that while you may have to take things a little slower and be a little braver yourself, they will soon feel like they can be themselves around you and will appreciate all the effort you made.

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