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I am currently studying in a high school, and I have several friends. Among them is a girl I like. We have several common interests e.g. gaming, and we're on very good terms and talk a bunch in real life and online. When I'm in a group, it's pretty easy to find topics to talk about; however, when I'm talking to her alone, there are often a few problems:

a) The conversation gets quite slow, and I run out of things to say. The silence gets quite awkward. b) If she makes small 'complaints', e.g. "I'm tired" or is happy about something trivial, I can't find anything to say to that. I sometimes end up just smiling awkwardly if the topic before was in some way funny.

Question: What can I do in the above situations? Where can I improve?

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    Do you find you typically have issues like this in any 1-on-1 conversations, or are these problems unique to your interactions with this girl? – Upper_Case Dec 13 '18 at 19:15
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a) The conversation gets quite slow, and I run out of things to say. The silence gets quite awkward.

Ask her questions.

I've had my share of both good conversations and bad while attempting to date. The ones that didn't go well typically went south because neither of us asked any questions. Conversely, I had a few start out poorly and turn around because one of us started asking questions.

But don't ask just any questions. Ask detailed questions that will require longer answers or lead to follow up questions. For example: instead of asking

Have you played any new games lately?

You should ask

What games have you been playing recently?

Asking specifically about what she is playing will open up opportunities for you to ask even more detailed questions about the specific games that she mentions.

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As you both are in high school there is lot to learn and explore things and this will help you for making an interesting conversation very often.

As you wrote that you two have common interests. Look for the thing in which you and she are interested to learn or planning to achieve a good reputation in that particular game or any field. Get your chess(for example) skills leveled up and help her with it to get her better too.

This way you most likely have unlimited chances to talk her very frequent or if you could find good point of her interest, she could start looking for you in her free time.

When you both get comfortable and enjoying being together, you could talk lot of things. :)

Conclusion: Improve your skills in a game or at any subject that you and she interested in, this would not only give you opportunities to talk with her but also you will be benefited by improving these skills in future.

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