Why is it so hard to initiate conversations?
Hello, and thank you for your question!
There could be a number of different factors that contribute to difficulty in either initiating or sustaining conversation with others, and without knowing a little bit more about you, your personality, your interests, etc., it's a little challenging to provide a precise answer to the situation you've described, so we'll dive into this from a more "general" perspective. Hopefully this will allow you to learn a bit more and, in knowing yourself as you do, may provide you with some "take-aways" that can point you in a more specific direction for future consideration.
1. Maybe You're an Introvert!
If you find that you're not all that into "small talk" and feel more energetically "recharged" from spending time by yourself, then it's quite possible you're an introverted personality type. Please don't think this means "antisocial" or "loner" -- introvert vs. extrovert (or even "ambivert") is simply a way of classifying how a person gets their energy.
Going forward on the idea that you may be of a more introverted personality type, introverts often find that their "internal world" is more interesting and/or contains more "depth" than many trappings of the external world (i.e., material things, who-did-what/who-said-what-to-who-and-why, etc.). The majority of the world's population is said to be of a more extroverted or ambivert (a little of both types) type. Many times, because of their differing perspectives on where they derive their energy and where their focus lies, introverts and extroverts have a difficult time conversing for very long. If the interaction is prolonged, the introvert often feels energetically depleted, as though they're conversationally being held "hostage" by the extrovert, and/or as though they've run out of things to say.
When two introverts happen to find each other in a situation where they're conversing about something, it's likely to be of considerable depth/meaning, and they likely will feel as though they understand each other. There will be little awkwardness in the conversation, and it will begin and end naturally.
If this resonates with you, do know that there is absolutely nothing wrong or dysfunctional with regard to being introverted; it's simply a difference in the way that apples and oranges are different, and know that any time we're going against our nature, we'll feel uncomfortable or out of place. Conversely, when we're being true to our nature, we'll feel very comfortable and at ease.
If you'd like to learn more about your personality type, consider checking out www.16personalities.com which is a free, online spin-off of the actual psychological assessment, then Myers-Briggs Personality Type Inventory (MBTI). There, you'll answer a series of questions that help determine your (likely) personality type, as well as many insightful articles that can help you learn more about yourself and others who are also your type. Many people find this kind of information not only enlightening, but reassuring.
2. Maybe You're Bored by Common Things
Usually starting conversations with strangers requires the identification of some commonality, which is then discussed. Many times, such things are obvious ("Nice weather we're having, eh?") or mundane ("Gee, parking around here is really hard to come by, huh?"), and may not provide enough interest to either party to continue the conversation beyond a "yeah" kind of reply.
If this resonates with you, you may want to consider finding events, places, etc. that you enjoy, which will increase your chances of coming into contact with someone who also has your interests, in which case it will be significantly easier to start and maintain a conversation, because the topics that are likely to come up will be of interest and meaning to you.
3. Maybe You're Asking Closed-Ended Questions
Much like the examples above in Item #2, if you're inadvertently asking closed-ended questions (questions that set the responding party up to provide a one-word, yes-or-no type of response), then there's not a whole lot that keeps the conversation going...and if a person continues to ask closed-ended questions, then it starts to feel less like a conversation (which is inherently back-and-forth) and more like an interrogation.
Here are some examples:
Closed-ended: "Nice weather we're having, eh?"
Open-ended: "What do you think of today's weather?"
Closed-ended: "Wow! Parking here sucks, right?!"
Open-ended: "Geez, what's a guy gotta do to get a parking space around here?"
Closed-ended: "Do you like cheese?"
Open-ended: "What's your favorite kind of cheese?"
4. Maybe You're Overly Self-Conscious
This is a common one for many people who are looking to branch out their social connections, especially if they're prone to anxious or depressive-type thought patterns (i.e., worrying excessively about things that might happen in the future and/or worrying about things that have happened in the past). We often think that other people are judging us, thinking critically about us, or that other people are thinking poorly of us/looking down on us, when the reality is that most people are more concerned about what *you're* thinking of *them* than what *they're* thinking of *you*. Most people are so preoccupied with their own insecurities that they don't have the mental "space" to be concerned with what you're doing.
When we're overly concerned about what others may or may not be thinking about us, it often serves as a strong inhibitor against acting like our authentic selves...which most people can pick up on (even if they can't put their finger on it), and they will feel vaguely uncomfortable, and want to leave the conversation. On the contrary, when we're fully present (i.e., not thinking about what they're thinking of us/the future and/or not worrying about things that have happened in the past that we can't control), we're able to respond to what's actually happening in the moment with a great degree of freedom and natural-ness/authenticity.
This may be a distinct possibility, particularly when trying to start a conversation with someone of the opposite sex, as you might be particularly concerned with their opinion of you and may be especially sensitive to rejection in that area.
The important thing to remember is that -- whoever you're wanting to spend time with socially -- they should accept you for *you.* (Of course, that means you actually have to *be* you in order for them to *accept* you.) If you feel uncomfortable around someone whilst being yourself; if they treat you disrespectfully whilst being yourself; or if they're asking you to change essential aspects of yourself in exchange for their friendship, then they're probably not worth your time. Having a true connection with someone based on a mutual sense of belongingness and acceptance is priceless...but you've got to risk feeling vulnerable at times in expressing who you truly are in order for someone to "see" you and accept you. And if they can't, don't or won't accept you for who you are, it's their loss and time for you to move on. :-)
5. You're Not Asking About Them
Sometimes an outgrowth of Item #4 above can be that a person becomes so self-conscious in conversation with strangers that they almost can't even *see* the person in front of them, so they end up talking only about themselves. Most people quickly get bored of that type of talk (as it's often very one-sided) and gives the appearance that the other person is selfish, inconsiderate, oblivious, full of themselves, etc., and most people are most comfortable in talking about themselves. So...if you want to have a conversation with someone that goes on and on, ask open-ended questions about the other person.
Example:
Conversation #1: "Oh my gosh...I've been so nervous about my presentation today! I studied all night, and hardly slept a wink. I'm absolutely exhausted. How does my tie look? Do you think plaid and stripes go together, or am I completely out of touch? My sister has told me I had no idea how to dress and I just..."
versus
Conversation #2: "What brings you to the presentation today? Have you always been interested in underwater basketweaving? Where did you first hear about it? What other hobbies do you have? How do you make time for them while working two full-time jobs and hand-raising baby llamas?"
As you can likely imagine, Conversation #1 will peter out pretty quickly, and may end with the other person either faking an excuse to leave the conversation, or simply (and rudely) disappearing while you're mid-sentence. Conversation #2, on the other hand could go on for hours, particularly if both people have some common interests.
One final tip: stay curious. Stay curious about yourself, the world around you, and others. Ask thoughtful questions that you truly care about the answers to. Be authentically you. Stay in the present moment and converse with others from that place.
Best wishes to you!