21 Conversation Starters for Long Distance Online Dating

Woman with Phone

Not sure what to say to someone you’ve never met? This can be an intimidating experience, whether you’re dating online or in-person. The conversation doesn’t have to be awkward if you know what to ask. Check out these conversation starters for long distance online dating.

Conversation Starters for Long Distance Online Dating

Here are some ideas about what to ask someone new online:

  1. How do you typically spend your time off?
  2. What has been your worst online dating experience so far?
  3. Do you consider yourself an introvert, an extrovert, or somewhere in between?
  4. What are your career goals, and what do you think it will take to achieve them?
  5. What kind of peer group were you a part of in grade school?
  6. What is your favorite childhood memory?
  7. Do you enjoy traveling? If so, where have you traveled and where would you like to travel?
  8. If there was a theme song or TV show that represented your life, what would it be?
  9. What does your morning or evening routine usually look like?
  10. Do you have any pets, or do you want pets in the future?
  11. What is your family structure like? (How many siblings, are you close to your family, etc.)
  12. Is there anything you read, watch or eat that you consider a guilty pleasure?
  13. If you could start a business and money was no object, what kind of business would it be?
  14. Do you believe in astrology? If so, what’s your zodiac sign?
  15. What’s something people assume about you that isn’t actually true?
  16. Who do you look up to most in life, or who motivates you?
  17. If you had to eat the same three meals every day of your life, what would they be?
  18. What is your biggest fear in a relationship?
  19. What made you decide to join this online dating site/dating app?
  20. What’s something obscure from your childhood that you don’t think many people know about? (Food, snack, cartoon, restaurant, etc.)
  21. What’s your favorite or least favorite part of your work day?

Consider these online dating conversation starters as a jumping point, but feel free to come up with your own! Think of questions you’d like someone to ask you or topics you’d like to discuss. The possibilities are endless.

How to Keep a Conversation Going and Avoid Awkward Silence

Whether you’re on a first date or talking to someone online, there may come a point when the conversation stops. This can feel awkward for both parties, and you may not know how to jumpstart the discussion.

For starters, avoid yes or no questions. This does not leave room for much discussion, and it forces you to come up with even more conversation starters. Rather than asking “Do you like {name of TV show}?”, you could say “Which TV shows are you currently watching?” The questions may arrive at similar answers, but the second version could open the door to multiple side discussions.

If you’ve reached a dead end with your conversation, bring up an interesting fact or personal story. This is something you can think of ahead of time so you don’t feel flustered in the moment. “Just the other day, I learned that…” This could encourage the other person to share in your interests/memories, or it may spark a new line of conversation.

You can always ask questions about the person’s interests or profession. “What made you get into this career?” “How long did it take for you to learn this hobby?” People are more likely to continue a conversation about something they’re passionate about, making these great conversation topics for long distance online dating.