How to Talk to Your Crush Even Though You Are Shy



Some people have absolutely no problem making conversation on a date or even with perfect strangers. However, many people admit to being shy, especially around people they don’t know or those who they’re interested in.

In my recent article, “Do You Talk Too Much On a First Date?” we looked at both the talkers and the quiet types. So for all of you who freeze up and don’t know what to say, I want to suggest practical ways to start up a conversation.

Many people have asked me for advice on how to break the awkwardness of going on a date or talking with someone they don’t know. Whether you are meeting a perfect stranger in a group setting or are on a date with someone you don’t know, the following questions will help to start conversation and keep it going. While these suggestions may seem simplistic and obvious, they’re a good place to start. (Obviously, the first couple will not apply to someone you are already on a date with).

  1. Say hello to the person.
  2. Introduce yourself with a smile. “Hi my name is _________.” After they give their name in return, shake their hand and say, nice to meet you. Look them in the eyes and smile.
  3. From there, you can take a couple different routes. Career or Fun. Let’s start with career since everyone knows that Americans like to talk about work. You might say, “So, what do you do for work?” “Oh, I’m a doctor.” You may follow up with, “Do you love your job?” Or, “Is this your dream job?”

If the answer is YES: “Wow, that’s great. What is it that you like about your job so much?” or “What made you want to go down that path?”

If the answer is NO: “Really? What is your dream job? If you could do anything, what would you like to do?”

These questions can potentially spark a good conversation and tell you a lot about the person in the process.

Every time a question is asked, listen closely while looking for those things you both have in common. If you both work in the medical field by chance, then you will have a lot to share and talk about. If you don’t, you will need to ask additional questions to understand her work more. If the person has manners, he will ask you what you do in return. Both sides should be interested in the other and be ready to share.

After you have finished the work topic, move onto the fun.

  1. “So, what do you like to do for fun? What are some of your hobbies and interests?” This is a great question because it tells a lot about a person. It is also one of the easiest ways to spark a good conversation and reveal potential compatibility. They may say, “I like the outdoors: hiking, camping, taking long bike rides, going to the beach, etc. I also like to play board games, or on occasion, to read a really good book.”

Again, it is important to listen to the other person and to find that common ground. For example, if you happen to like any or all of those outdoor activities, you will probably have a lot to talk about. “Oh really, I like hiking too… How often do you go? What’s your favorite place, and why?”

Asking open ended questions are always more beneficial. Or, perhaps maybe you love books, and while he or she only likes a good book occasionally, it’s still a topic to cultivate. Each topic you embark on is a potentially good conversation in the making. After these topics start to dissipate, if the person is polite and cares about you, they will ask these same questions or others in return. “So, what do you like to do?” This will bring about another list of likes and another round of lively conversations.

Some people will connect right away, which is ideal. Others, won’t click with right away, but will after a time. A relationship may grow and become more comfortable.

But at the same time there may be others who have no connection and conversation is difficult even with these questions. Most likely, these aren’t the people you will be compatible with. Making good conversation is an art that doesn’t come easy for everyone, but the more you do it, the easier it becomes, and the more you cultivate an important skill needed for the rest of your life.

What opening questions do you ask on a first date or in a first interaction? I would love to hear the ideas that worked for you. Feel free to add them in the comments below.



  1. Dave-868059 February 7, 2015 Reply

    Some truth here. Overall I enjoyed reading this article. In my opinion, Compatibility is key as some couples have ‘chemistry’ from the onset, shy or not, and some just never will no matter how hard they try. Polite conversation, yes, advancing beyond that, probably not.

  2. Bill-304473 November 16, 2014 Reply

    In speaking to a woman one has a great interest in, the difficulty is simply fear of rejection. He does not want the rejection by this one person in particular. At an elder age, I find talking to women, about any subject, much simpler. Maybe it’s because how she responds means nothing to me. I am too old for a developing any close relationship. Another factor is that I feel the person will not think I’m showing interest in anything sexual. Thus, she will converse , knowing it’s nothing special (by me and her). We’re in different generations. Anyway , the reason we clam up is simply fear of rejection.

  3. Nathan-1037594 October 15, 2014 Reply

    I am thinking best way to be prepared is making a list of several leading questions in my phone and then have questiins Id ask based on their answers like if they say they hate their job I might say I had a job once I didn’t like too much or I knew a friend who experienced this and they felt… Would try to have a general idea of what questions are in my mind and then ask a few questions based on what other person is asking or seems Intersted in. Would sort of be like an outline for a speech or a novel and gives you cues you need to remember what you have to say.

  4. Joe-1141122 October 14, 2014 Reply

    As a guy who is debilitatingly shy, it is far more difficult to get past it then this article states. For instance, where I go to church there is a woman about my age (early 30’s for her mid 30’s for me) that I find very attractive. She’s physically attractive but her devotion to her faith and her enthusiastic profession of her faith is what I find so attractive about her. I’ve been going there for three years now and barely gotten past hi. I would love to see if there is mutual interest but my shyness always finds a way to stop me from doing anything.

    • Nathan-1037594 October 15, 2014 Reply

      Yeah it’s tough when your really trying hard to make a good impression. I find in these situations I try so hard to say the right thing I just lock up and forget what I have to say. I guess sometimes you just have to be willing to throw your net out there, and see where things lead. Perhaps you need to also do a little investigating and closely observe how she prays, how she crosses herself, how she receives the echirist ,as these small details tell a lot about a person. They also help to identify her personality and what may like or

    • Miles-814 March 13, 2015 Reply

      Joe, I am no expert on this, really. I have been in your shoes before. However, if there is one thing I have learned about women is that they prefer to get to know a guy over time. If she is a regular mass-goer, she is going to like the fact that you go to mass, too. So, that is a plus in your favor. One thing you want to avoid is wasting time with a woman that might never be interested in you. The sooner you figure out where she stands, the better. There are many things I have noticed that seem to work pretty well. 1) Asking short simple questions about things that nothing to do with her is an easy way to get things started. You might ask ask a prompting question that might allow her to feel comfortable telling you a little bit about herself, with your asking her anything about her: “Hello! I am a single Catholic guy, and was just wondering if you knew of any young adult groups within our diocese?” If she answers respectfully, in the future, you can occasionally tell her about young adult events that, either, you have been to OR about events that are coming up. You can hand her a flyer for a really good young adult event, too. Also a question like that might prompt her to tell you that she, too, is not taken, as well. Just a thought. Girls, please feel free to add or adjust this to make it more to your liking.

  5. Jose-1017468 August 8, 2014 Reply

    Interesting article and it can be hard to think of what to say when you are trying to talk to that woman that sparked your interest. Regardless of being shy, you definitely can’t forget about those women that will judge you based on your looks and perhaps the type of job you have with how successful you will be when you take initiative to talk to a woman. Not that I am saying all are like that but there are those that are.

    • Cindy-943596 August 8, 2014 Reply

      When I read this portion of the article I was thinking the same thing. Would he think that I am trying to judge him on what he does for a living. I am actually interested in what people do. It is just a safe icebreaker. You will be able to tell right away if the person asking is truly interested in knowing a little bit about you, or just looking for a particular financial/social status before getting to know who you are as a person. I love my job and would hope that the person I am talking to will ask what I do.

  6. Richard-15378 August 7, 2014 Reply

    Odd that there is a pic of a beautiful woman, as if she has something to ever be shy about ….

  7. Ann-69118 August 6, 2014 Reply

    Being shy can be a hard thing to over come. I used to be there so I know how it is. I over came shyness by putting myself out there and trying things sure it’s hard but the rewards far outweigh the risks.

  8. Michael-410923 August 5, 2014 Reply

    Interesting article (as well as the previous). Someone writing ‘I like guys who make me laugh’ may induce a great effort to entertain, to little avail.

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