The 10 Best Dating Tips for Shy Guys – Learn from My Mistakes

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Your shyness isn’t your fate. Even self-conscious men may be popular with females. Step outside your comfort zone and adhere to the dating tips for shy guys which are mentioned in the article below.

I’m sharing my experience because I’ve risen from a bashful boy who couldn’t say a word to a girl on the first date to a confident and charismatic man whom women are crazy about.

Ask Questions

This is extremely useful and efficient advice which shows excellent results during dates with the opposite sex. First off, when you’re anxious and nervous, it’s difficult to keep up a conversation. Sometimes guys start talking too much about themselves without paying any interest towards their partner. Or worse, they’re just sitting in silence not saying a word. In this situation asking questions will allow you to relieve tension and show the girlfriend that you’re focused on her personality.

Asking questions will provide you with dozens of topics for further communication. You may find out about your shared interests, hobbies, and so on. It will be much easier to talk with each other later.

Some questions you may ask even on the first date:

  • What are your hobbies?
  • Which is your favorite country you’ve ever visited?
  • Do you have any pets? Tell something about them.
  • What is something you’re proud of?

Talk About a Common Interest

This tip follows from the previous one. After asking questions you get to know each other closer and easily detect mutual interests. It would be perfect if you have some common hobbies, movies or activities you both like. Actually, this advice stands out from the other dating tips for shy guys on a first date due to your mutual engagement in the conversation and discussing things you admire.

My advice here is not to argue with your partner even if your opinions about something are different. Remember, that the task isn’t to prove your point. The aim is to build a pleasant, peaceful, and interesting dialogue that will lead to the establishment of closer relationships.

Give Compliments

We cannot but mention making compliments. This is a clever trick ‘cause you must be brave enough to praise the significant other for something. Be sure she will be pleased and maybe even blushed.

As a timid man, you can think about some unique expressions in advance or use our examples. The only thing you should avoid is cliche. Women won’t appreciate banal phrases which you can say to any girl in the street. That’s why you should forget about “You’re beautiful” or “You look stunning” or whatever. Find something special in her appearance or, even better, in character and praise her for this. You must make your partner feel special. Depending on the situation you may try the following examples:

  • Your sense of humor is as good as your taste in art.
  • You’re an ideal girl, cause your mind is just as sexy as your beauty.
  • I miss your smile.

Make Jokes

This is a secret weapon among other dating tips for shy guys. Our experience suggests that nerds aren’t interesting to ladies. Women are attached to sociable, outgoing charismatic men with a good sense of fun. That is why if you manage to motivate your girlfriend to laugh or at least smile, we assure you that the date is on the right path.

Of course, while discussing serious topics there is no place for jokes. You should feel the moment and make jokes depending on the situation. If you’re not so good at making jokes, think about some funny stories from your life that can bring a smile to your girlfriend’s face.

Show What You Want

This advice is also a small hint for bashful guys who have a lack of self-assurance. To have more than one date with a potential fiancee you should take initiative on your own. When it comes to dating tips for shy guys on a first date, this advice is really valuable.

Don’t expect a girl to ask you for a next date. Suggest her ideas for further appointments, places you can visit together, or different options of joyful pastimes. Let your significant other feels like a vulnerable girl.

Clarify that you’ve enjoyed the initial date and it would be great to meet again asap. Express your feelings and emotions. We bet that women appreciate genuine men. By showing your intentions you’ll be brimming with confidence in her eyes.

Fake It Until You Make It

While discussing dating tips for shy guys, we must mention again that ladies do much appreciate self-assurance in men. And if you’re short of this trait, you must try to acquire it.

Don’t get me wrong, you shouldn’t pretend to be a person that you’re not. At first, being sure of yourself can be your habit when you’re flirting with girls and aiming to allure them. As we all know, acquiring habits is a time-consuming process that requires effort. That’s why you must be ready to leave your comfort zone and to be open to something new.

Even if you’re a shy person, by acting confidently you’ll feel sooner or later that confidence has transformed into your natural trait. Such things as smiling, taking initiative on your own, making compliments, and other suggestions from our guide will allow you to fake confidence and to become a self-assured man in the eyes of your sweetheart.

Use a Matchmaking Service and/or Go Speed Dating

The list of offline and online dating tips for shy guys won’t be full without referring to matchmaking services together with speed dating. Cooperation with a matchmaker is a perfect option for timid guys because everything will be arranged for them by a professional. Remember “Hitch” starring Will Smith? The main character is a “date doctor” who helps shy men to allure women. That is the thing how matchmakers work in general.

For example, we get in contact with the client, identify all his wishes and preferences in women. Then we do our best to find an ideal match for him.

The second option you may try is speed dating. Its big advantage is limited time for a dialogue with girls, thus there is no place for awkward silence and shyness. You must hook girls in three-eight minutes. Actually, speed dating trains you to leave a comfort zone and to become a more outgoing person.

Try Active Dates

If you’re afraid of uncomfortable silence during a date in a restaurant or somewhere else, try dates combined with activities. It can be a bike ride, a class of cooking, or any other common hobby you both are into.

In this case, you’ll always have what to discuss. Sometimes people are so engaged in the process that they don’t even have time for conversations. The discussion of the active date will be later and be sure you’ll be full of emotions and you’ll have what to chatter about.

Make a Social Warm Up Before a Date

Whether you’re preparing for a workout or a date with a girlfriend, a warm-up is always a useful thing. Of course, it’s different warm-ups, but the idea is the same — to get into special conditions. While discussing dating tips for shy guys on the first date, you should limber up socially.

What does it mean? To avoid embarrassing moments when you swallow your tongue not knowing how to lead a conversation with your partner you can practice “small talks” with somebody from your social circle. This exercise will let you relax and believe in yourself before a date.

Embrace Your Shyness

To tell the truth, shyness isn’t a big problem. Many ladies would prefer a calm and bashful guy to an arrogant and hard-headed man because the first is considered to be more sensual and loving. Many protagonists in romantic movies are quite shy men.

If you are embarrassed in front of a woman, it means that you really like her. Thus, if you manage to deal with your shyness and make an appointment for a date, you’ll be a hero in her eyes who has got over his fears.


Being a timid man doesn’t mean it’s a disaster. Actually, you can handle everything if you use our dating tips for shy guys. Remember that you’re responsible for your life. Building a healthy relationship with a beloved woman is worth overcoming your shyness.

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