Matty,
Instead of talking to fill the silence, ask a question and get her to help fill the silence.

There are two types of questions that work well in this situation: questions that require multi-sentence answers, or questions that lead to more questions.

Let’s say I’m talking to someone that I don’t know well. I can ask, “How is your week going?” or “How was your weekend?” She may give a multi-sentence answer, or she may give a short answer. A short answer will be some version of “Good” or “Bad”. Even if she says “Okay”, her tone of voice will probably suggest that it’s good or bad.

Let’s say she had a good weekend. You can ask her “What did you do?” or “What happened?” in a tone of voice that makes you sound like you’re interested in the answer. If she had a bad weekend, you can ask her “What went wrong?” or “What happened?” in a tone of voice that makes you sound like you’re concerned. (It helps if you really are interested or concerned, but you should sound that way even if you’re not.)

Pay attention to each answer she gives, because it can lead to another question.

Sometimes she’ll answer your question with a short answer and a question of her own: “My weekend was good. How was yours?” Instead of using this as an excuse to launch into a long monologue about your weekend, you can turn it around: “My weekend was busy but fun. What did you do?”

It’s considered good form to remember some of the things she says in one conversation so you can bring them up in a later conversation. If she tells you she’s going to the beach with her best friend, you can ask her how the beach was after that trip.

And practice being a good conversationalist with everyone … not just girls you’re interested in.

I had a similar problem when I was your age. The solution takes a lot of practice, but it is fairly simple. Ask the other person questions.

If you still get a lot of awkward silences that person is not a good fit for you. Enjoy the date if you can’t cut it short and move on.

After reading this, I feel more encouraged to sit and listen and ask my (horrible) questions.. but when it gets silent, my mouth is going to open and whether or not it’s going to stop decides on you.

I am not sure that I agree with Erika regarding “I’m sorry, I’m not finished yet” comment. That can come off as cold and rude… It has to be played right, and with a common level of trust which generally isn’t there on a first date…

There are a few things you can say to someone to gently remind them that conversation is a two-way street.

The first one is to say flirtatiously, “Enough about you, now back to me!”

The other thing to do, when someone interrupts you before you are finished, is to say, “I’m sorry, but I wasn’t finished.”

Keep doing that until they get the point.

If it’s said the right way, it will clue the other person in on what a clod they’ve been.

Let’s say everything about your being (personality, past experiences…) dictates that for you, the optimal energy for any interpersonal interaction is a value of 10. For you the equation is x + y = 10. So you’re x, and the other person supplies the y. If your date’s y is a 7, then you respond with a 3 to bring the energy of the conversation to the level at which you’re most comfortable. 7 + 3 = 10, right. If however, you’re with a more mellow talker who gives off a 2 (in terms of stuff like volume of voice, expressions, gestures and openness of discussion content) you may feel the need to bring an 8 to the exchange to once again have everything add up to a 10.

(We’ll ignore the fact for now that there are seemingly infinite variables that can confound the quality of an exchange. eg. a person’s ideal comfort level may not be the same as your 10, but a 25, and you don’t even have it in you to go above 10. Or a person may have less precise control of his energy spigot, so he wants to give off a 9 but only succeeds at producing a 6. Then the whole equation changes again when there are more than 2 people involved in an interaction.)

Anyway, my point is that the men you date may be just doing this algebra and may perceive you as a 2, which is why they’re bringing their 8 game to the table. And maybe we can take this one step further and say that social compatibility ideally looks something like 5+5 =10.

Or maybe it’s a good thing that Evan is the one who writes dating advice for a living because in hindsight, my “theory” seems only nominally useful as a metaphor.

Keep up the good work Evan, because people will always need you to explain things more plainly than I just did. .

People have different colloquial styles. To extend Evan’s tennis analogy… some expect conversation to be a polite, gentle rally – “your turn, then my turn, ewld chap”. Others, like the guys you’ve been going out with apparently, barely wait for the ball to make it onto their side of the net before they come charging back at it with an overhead smash. It doesn’t necessarily indicate a character flaw if a person expects you to play a little more offense.

Maybe the fact that you’re both playing a different game signals you’re incompatible . Or perhaps it may simply mean you could bring a little more energy to the conversation.

It amazes me that that anyone over the age of 18 would not have figured out how rude and boring it is to engage in monologue conversations. Personally, I suggest not wasting your time, ever, with someone who goes on and on about themselves. One date is more than enough with that type.