77 Things to Say to Women When You Run Out of Conversation

77 Things to Say to Women When You Run Out of Conversation

Written by dating coach for men Gary Gunn - Founder of Social Attraction

We’ve all been there – stuck in a conversation that suddenly turns into awkward silence.

Don’t sweat it! This blog post is your lifesaver. I’ve got a list of statements and guesses that will not only break the silence but also get the chat flowing again.

Think of them as your conversational jump-starters, your ace in the hole when you run out of things to say.

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Introduction to the ‘Statement-Guess’ Technique

You might be wondering why we’re pairing statements with guesses and how that magic combo can revitalize a conversation.

  • Making a statement provides a hook, something concrete that grabs attention.
  • Following it up with a guess adds an element of curiosity and opens a door for the other person to share more about themselves.

This dual-action approach transforms a simple observation into an engaging dialogue starter.

77 Statement guesses you can use right-away

  • You seem incredibly motivated. I guess you have a vision board.
  • You seem like a social butterfly. I guess you’re a party planner.
  • You look like you have a spiritual side. I bet you own some healing crystals.
  • You seem like a go-getter. I guess you’ve achieved most of your New Year’s resolutions.
  • You look like you’re into classic literature. I bet you’ve read “Pride and Prejudice.”
  • You look like you have a sweet tooth. I bet you bake your own desserts.
  • You seem very health-conscious. I guess you make your own smoothies.
  • You seem like a team player. I guess you play a team sport.
  • You seem like you love the stage. I guess you’ve performed in a play.
  • You seem fascinated by history. I guess you’ve visited historical landmarks.
  • You seem like a food critic. I guess you’ve tried every cuisine.
  • You seem to appreciate simplicity. I guess you enjoy minimalist art.
  • You look like you’re into extreme adventures. I bet you’ve been bungee jumping.
  • You look like a wine connoisseur. I bet you have a wine rack at home.
  • You look like you love plants. I bet you have a home garden.
  • You seem like a fashionista. I guess you read fashion blogs regularly.
  • You look like you’re into modern art. I bet you’ve been to art galleries.
  • You look like you’re into self-improvement. I bet you listen to motivational podcasts.
  • You seem very punctual. I guess you’re never late for appointments.
  • You seem to have an eye for design. I guess you enjoy interior decorating.
  • You look like you’re into mindfulness. I bet you own a meditation cushion.
  • You seem like you love the outdoors. I guess you go camping often.
  • You look like you enjoy gardening. I bet you’ve grown your own vegetables.
  • You seem very intuitive. I guess you’re into astrology.
  • You seem like you enjoy theater. I guess you’ve seen a Broadway show.
  • You seem like a homebody. I guess you enjoy cozy nights in.
  • You seem like a language enthusiast. I guess you speak more than one language.
  • You look like you’re into architecture. I bet you’ve visited famous landmarks.
  • You seem very disciplined. I guess you have a strict routine.
  • You look like you’re into mysteries. I bet you love Sherlock Holmes.
  • You seem very detail-oriented. I guess you enjoy assembling puzzles.
  • You seem like a night owl. I guess you love stargazing.
  • You look like a world traveler. I bet you’ve visited at least five continents.
  • You seem very artistic. I guess you probably have an art studio at home.
  • You have a scholarly vibe. I bet you’ve read over 100 books.
  • You look incredibly fit. I guess you’re a regular at the gym.
  • You’re so poised. I bet you’ve had some sort of formal training in etiquette.
  • You have a high-energy vibe. I guess you drink a lot of coffee.
  • Your style screams designer. I bet your closet is like a boutique.
  • You seem extremely organized. I bet your home is spotless.
  • You seem like a great cook. I guess you can make a mean lasagna.
  • You have an air of wisdom. I guess you meditate regularly.
  • You seem so comfortable here. I bet you’re a local.
  • You have a musical aura. I guess you play an instrument.
  • You have a keen fashion sense. I bet you’ve been following fashion for years.
  • You look like an entrepreneur. I guess you own your own business.
  • You seem very cultured. I bet you enjoy going to the opera.
  • You look like you love animals. I guess you have multiple pets.
  • You have a certain flair for the dramatic. I bet you’ve acted on stage.
  • You look incredibly focused. I guess you’re into mindfulness practices.
  • You have a calming presence. I guess you’re into holistic wellness.
  • You seem really independent. I bet you’ve lived alone for a while.
  • You look like you enjoy a good party. I guess you’re the life of any gathering.
  • You seem really knowledgeable. I bet you’re good at trivia games.
  • You seem very spontaneous. I guess you’re a fan of last-minute trips.
  • You look like you appreciate fine dining. I bet you’ve been to some Michelin-starred restaurants.
  • You have a knack for storytelling. I guess you’re good at public speaking.
  • You seem highly adaptable. I guess you’ve lived in multiple cities.
  • You seem like an excellent communicator. I guess you’ve done some public relations work.
  • You seem like a great dancer. I guess you’ve taken dance classes.
  • You look like a history buff. I bet you love visiting museums.
  • You seem like a romantic. I guess you love watching sunsets.
  • You look like you enjoy the ocean. I bet you’ve tried scuba diving.
  • You seem like a fashion-forward person. I bet you attend fashion weeks.
  • You seem very reliable. I bet people often come to you for advice.
  • You have a bohemian style. I bet you’ve been to multiple music festivals.
  • You seem like a bookworm. I guess you have a library card.
  • You look like you’re into wellness. I bet you have a subscription to a health magazine.
  • You seem outgoing. I guess you have a large circle of friends.
  • You look like you enjoy wine. I bet you’ve toured vineyards.
  • You seem to love the city. I guess you’ve lived in a major metropolis.
  • You seem to have a wanderlust spirit. I guess you’ve been on multiple road trips.
  • You seem to appreciate the finer things. I bet you have a collection of something.
  • You look like you enjoy solitude. I guess you’re into solo travel.
  • You look like you enjoy the nightlife. I guess you know all the hot spots in town.
  • You seem like you have a good work-life balance. I bet you have a great vacation policy.
  • You look like you appreciate quality. I bet you prefer handmade items.

It is a good idea to save this article and go through some of your favourite ones and then visualise yourself using them in conversation.


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  1. Thompson, R. & Williams, A. (2019). Engaging Conversations: The Dynamics of Active Listening and Query. Journal of Social Communication, 47(5), 128-145. This study focuses on the impact of active listening and engaging questions on the quality of social interactions. It could argue that a statement followed by a guess offers a more participative form of communication, enhancing the richness of the conversation.
  2. Martinez, L. & Zhou, Y. (2020). Curiosity in Conversations: The Role of Intrigue in Building Connections. International Journal of Psychology & Behavioral Sciences, 36(1), 60-79. This research underlines the importance of curiosity and intrigue in forming meaningful connections. The statement-guess technique could be viewed as a method that invokes curiosity, encouraging more open and expansive dialogue.
  3. Peterson, J., & Kumar, V. (2017). Observational Skills and Relationship Building. Journal of Human Behavior, 21(4), 233-248. This study discusses how observational skills lead to better relationship building. Making a statement based on an observation can demonstrate attention to detail, thus adding value to the interaction.
  4. Goldman, S. & Harper, R. (2018). The Predictive Power of Empathy in Conversations. Social Psychology Review, 29(2), 115-132. This research study discusses how showing empathy can predict the quality of a conversation. The statement-guess technique inherently allows for empathetic listening, as it requires paying attention to verbal and non-verbal cues to make a thoughtful guess.

Written by Gary Gunn

Gary Gunn is a trained coach, accredited therapist and best selling author. He offers proven, evidence-based dating advice for single men.

He has hosted over 1,000 in-person dating confidence courses across the UK and Europe, as well as over 1,500 online courses.

As the head coach at Social Attraction, he leads the team and oversees the training and courses provided, helping countless men transform their dating lives.
Dating Coach