How to stop running out of things to say when talking to her

A long time ago, I remember trying to start a conversation with a woman who I thought looked kinda cute. It went something like this…



“How are you?”

“I’m good. How are you?”

“Good, good.”


(Uh-oh, awkward silence! How do I keep the conversation going? What do I say next? Do I make a joke? Should I comment on how she looks? Think, Steve, think!!)

“So, the weather’s pretty nice,” I muttered. (The weather? Really Steve??)

“Yeah,” she replied.


“Umm, I need to go,” she finally said. “Nice talking to you” she halfheartedly added. Well, crap. It only took me about 30 seconds before I completely ran out of things to say to her.

How do you overcome the obstacle of running out of things to say when talking to women?

1) Encourage her to talk about herself

As Dale Carnegie writes in How to Win Friends and Influence People, being a good conversationalist involves talking in terms of the other person’s interests and listening to them when they talk about themselves. Try to find something that she would be interested in telling you about herself. Maybe she has a hobby that she would enjoy telling you about? Maybe she has a cool story from her past? Show her that you’re interested in her opinions, backstories, and feelings and she might talk your ear off.

If she’s telling you about herself, show her that you’re listening with your body language. Nod your head from time to time. Make eye contact. Give her an occasional “Mhmm” and lean in toward her if you’re both sitting down. Ask a few follow-up questions. Don’t interrupt her and make sure she’s absolutely done talking about herself before changing the subject.

2) Look for things you have in common

Try to find something that the two of you are passionate about or have in common. Maybe you’re both readers? Have the same hobby? Taste in music? Know the same person?

Once upon a time, I was at a weekly gaming meetup held close to where I lived and I met this cute, quiet woman wearing a pair of glasses. (Back then, finding a nerdy woman who was into games was like hitting the jackpot for me.) After I introduced myself to her, she started by admitting that she was somewhat of a quiet person and that she hoped I didn’t mind.

As it turns out, we ended up talking for almost an hour.

We quickly realized that we had a lot of the same geeky tastes. She told me how excited she was for the newest Pirates of the Caribbean movie to hit theaters and how she was anxiously waiting for the newest Harry Potter book to be released and how Yoshi is the coolest video game character ever. From there, the conversation flowed effortlessly.

By the way, I sometimes see people worry about their relationships because they don’t have much in common with the person they’re dating. It’s not 100% necessary to have a lot of things in common with a woman in order to get along with her. Rami Fu from Gutsy Geek writes that having shared values is more important than having shared hobbies or interests.

Things that you have in common with her is low-hanging fruit. It’s not the end of the world if the two of you are like night and day, but if that fruit is within reach then go for it.

3) Use conversational hooks to shift into related topics

As she’s talking to you, look for conversational hooks that you can grab on to and shift into related topics. Say that you’re talking to a woman and she’s tells you…

“I love playing basketball. When I was in middle school, I would get together with the boys and play with them all the time. They would always expect to beat me because I was a girl. Which made it feel really satisfying whenever I won.”

From here, there’s a bunch of directions that you could take the conversation. You could talk about…

  • Any sports you like
  • What you enjoyed doing when you were little
  • Your experiences from grade school
  • A time when you triumphed even though you were expected to lose

These are all perfectly good directions to take the conversation. When you learn to recognize these conversational hooks and to use them as you talk to her, you’ll be able to continue any conversation indefinitely.

4) Follow up after answering questions about yourself

This is something that I used to screw up all the time. And it wasn’t until I had a woman tell me that she didn’t want to go on a second date with me specifically because I wasn’t doing this that I realized how bad I was.

If she asks you questions about yourself, don’t just answer her question. Follow up on your answer! For example, if she asks you…

“Do you like to travel?”

…you could reply “yes” or “no”. However, if you don’t expand on your answer then you’ll come off as boring. She could get the same amount of intellectual stimulation by asking a Magic 8-Ball the same question.

Instead, follow it up with an insight. You might say:

“I love traveling! Last year, I went to China and had a great time seeing the Terra Cotta army. It’s amazing how much history there is.”

Open-ended questions about yourself should also be followed-up upon. If she asks you “What’s your favorite movie?” you could say “Toy Story”. However, if you just leave it at that then the conversation tends to die down.

Instead, follow it up with an insight. You might say “When I was little, I really loved imaging that my toys could come to life when I left the room. And I grew up parallel to Andy, so when he gives away his toys at the end of the third movie it really feels like your childhood has come to a bittersweet close.”

5) Have a few stories prepared

Finally, a great way to add value to a conversation is to have a few good stories in your back pocket. You can transition into a story by using a script such as

“That reminds me of a time when…”
“By the way, something interesting happened to me the other day…”

Your stories don’t necessarily have to be related to what you were just talking about. Telling a completely unrelated story is a great way to change the topic to something more interesting if the current conversational thread is beginning to wind down.

Personally, it’s hard for me to come up stories on the spot. Even more so if I’m romantically interested in her and I’m totally nervous on the inside. That’s why I recommend preparing your stories beforehand. Practice them a few times and try testing them out in a low-stakes environment by telling them to a friend or co-worker to make sure that you get the reactions you’re hoping for.

I used to struggle with storytelling a lot because I used to think that I was not an interesting person. After all, I work an ordinary 9-to-5 job where every day is almost exactly the same as the day before. How interesting could I possibly be?

As it turns out, I had a bunch of interesting stories I could tell about myself. That’s because how you tell a story matters at least as much as what the story is about. Even if you have an “ordinary” job and you have “mundane” hobbies, you can make your stories interesting by adding a twist or by making it relatable to your audience.

This is why Star Wars The Empire Strikes Back is widely regarded to be much better than Return of the Jedi. Even though Return of the Jedi had a bigger adventure and higher stakes, the tension and emotional impact of The Empire Strikes Back felt much more real because of the way the story was told. Luke and Darth Vader’s battle was much more tense than the battles involving the Ewoks.

Ewoks are cute and all, but this was much more tense than anything in Return of the Jedi

Making your own luck

One final note. If she’s consistently giving you short or curt responses whenever you say something to her then it’s possible that she’s just not interested in you. Sometimes it’s just due to factors beyond your control. If she has wildly different tastes in men than you can provide or if she’s not emotionally ready to date anyone then there’s not much you can do about it.

There’s always an element of luck involved when it comes to dating. Don’t get discouraged if things are not working out from time to time! Keep practicing the above five practices as you talk to women and you just might find your luck starting to improve.

In addition to everything listed above, I have a bunch more scripts to help you talk to women in The Quietly Romantic Guide to Talking to Women. Enter your email below and I’ll send it your way!

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