If you’re going to try your luck at online dating, you need the ability to start a conversation and ask interesting questions.
The most important thing is to go into online dating without expectations. Have fun and don’t make rejection personal.
It might take a while to find that perfect match. Just let things happen naturally and don’t try to force it.
Some General Advice
Humor is King
I believe humor is always the best approach, but sometimes it’s hard to communicate humor online.
Setting up your online dating profile to showcase your goofy side will make fun questions more relatable.
If your profile makes you seem square, you might be better off with a more sincere approach, but be forewarned, women rarely want to see your serious side in the early stages. I highly recommend keeping things light in the beginning.
Whenever starting a conversation, try to ask an open-ended question. Avoid yes or no questions and avoid questions that get deep or get personal.
Some guys try to use outlandish lines to get a reaction, and although that works sometimes, it’s cheap and rarely gets you the date. Ask funny questions, but don’t be a clown. Being real always works better.
Read: How To Find Common Ground With a Woman
Don’t Be too Eager
A lot of guys go straight for the date.
That might work sometimes, but in my experience, the best way to get the date is to let an organic conversation develop into witty banter.
Don’t ask 3 questions and then go straight to asking her out. Give it time. Show her that you’re a decent guy and that you can hold a conversation. If you learn how to consistently make an excellent first impression, the right person will come.
Success from 100 No’s
Online dating can be kind of like sales. It might take 100 rejections to get that one yes. DON’T TAKE THINGS PERSONALLY.
You have no idea what’s going on in a woman’s life. Don’t blow it up because you haven’t heard back for a week or two. That’s a huge red flag and will never bring a positive result. Maybe she met another date right before you and she’s seeing where that goes first. Maybe she’s taking a break from the app. Maybe she’s trying a different app. It’s not always about you; the worst thing you can do is go off the rails and ruin a future opportunity.
Also, try to remember that people like different things. You’re not going to be everyone’s cup of tea. Embrace the rejections like a gentleman and move on.
If you stay cool, the yes will come.
Value the Slow Play
I can’t tell you how many times a match has been formed that fizzled out, just to pick up months later. It is a HUGE mistake to overplay the situation just because you lose patience. Keep your cool and ALWAYS leave things open-ended. She might be having fun with her current date, but in a few months, that could be you. Don’t burn the bridge just because you’re desperate to get laid.
Know What You’re Searching For
If you have a vision for what you want, you’ll have better success when using online dating apps. Some women are looking for a long-term relationship, some are looking for something quick and dirty. If you signed up looking for love, you better know what you want in a potential partner, and don’t be afraid to make that known after some light conversations.
If you don’t have the guts to be upfront about your intentions, you’ll have a miserable time in the dating world.
You’re Flirting, Not Making Friends
Whatever questions you’re asking, make sure to take a flirty approach. Conversations will naturally offer up opportunities to poke fun and use humor. Don’t be boring, and don’t be afraid to ask flirty questions.
Here’s my list of the 50 best questions for online dating.
Disclaimer: Not all of these are openers. This is more of a general stockpile of questions you can ask to keep the conversations moving.
1. What’s your go-to karaoke song?
Knowing a woman’s karaoke song can tell you a lot about her personality and it presents opportunities to poke fun and flirt.
2. What’s the craziest thing that’s happened to you on a date?
This question can take the conversation in lots of different directions, but it’s not dull, and boring is the worst thing you can be.
3. What’s the best thing you learned from your last relationship?
I recommend keeping the online chit-chat short and sweet, but some women need more time to get comfortable and build a connection. This is good for those situations.
4. What’s your favorite song right now?
It’s the recency of the question that makes it so good. It’s much easier to think of your favorite song right now vs your favorite song of all time. It also tells you what kind of music they like and can help you to understand their personality better.
5. Who in your family inspires you and why?
One time I communicated back and forth with a woman for 6 months on Tinder before we met in person. We ended up dating for 6 months. You rarely want to get this deep, but this is a good question for those more sentimental conversations.
6. Dogs or cats?
Honestly though, if she says cats, bail.
7. What’s been your favorite adventure?
I LOVE this question. This will show the coolest sides of people. It’s something people can enjoy telling you about and opens up a really great conversation. Use this one as an opener.
8. Favorite album from your childhood?
Another solid opener for people in a similar age demographic. Connecting over music is always a good thing.
9. Apple or Android?
Say no to green texts.
10. What was your first job?
This can be good if you have a funny response in the chamber. After she answers, she’ll ask you about your first job. Have a funny story prepared.
11. City lights or country stars?
A strong opener and it hits home for a lot of people.
12. Early bird or night owl?
Not a good conversation starter, but easy to throw in mid-conversation.
13. Lake or ocean?
After she answers, she’ll most likely ask you the same question. For example, “I love the lake because of the water sports. Have you ever been wake surfing?” In one answer you’ve signaled that you have a fun life experience and that you’re athletic enough to wake surf. Her subconscious is slowly profiling you and checking boxes.
14. Who is your adult idol?
Drop this question at any time during the conversation. The answer will tell you a lot about the person.
15. What’s your favorite fun fact?
Make sure you have a fun fact ready too!
16. Where’s the number one place you want to visit?
Once she answers you can respond with, “I love it. I’ll get us tickets if our first date goes well”. She’ll know you’re being sarcastic, or are you?
17. Have you ever been in love?
Save this one for the long and sappy convos. Make sure it’s a connection worth your time because now you’re getting invested.
18. What’s something you’ve done that was on your bucket list?
Fun question with exciting answers.
19. Have you ever had your heart broken?
This question is good if you respond to her answer with something funny. Try to be clever and show that you can make her smile.
20. Weed or alcohol?
Does she like to stay in and chill or go out and dance? Now you know!
21. What’s the worst date you’ve ever been on?
This usually provides a fun story and is a great way to learn what not to do.
22. What’s your favorite junk tv show?
I haven’t met a girl that doesn’t watch a little reality TV in her free time. Chances are if you start dating, you’ll be watching that show too!
23. What’s your favorite movie?
If she answers Star Wars, marry her.
24. What’s your ideal weekend look like?
This is a great question to learn about a woman’s personality and hobbies.
25. What plans are you most looking forward to right now?
It’s important to have fun plans for your future. It gives you something to daydream about when you’re stuck at work. This is an easy way to get her talking about something that will put her in a good mood.
26. Is the glass half empty or half full?
If you want to live a happy life, avoid pessimistic people. Positivity wins every time.
27. Do you have a hidden talent?
Some girls will have a funny answer, and some will respond with something kinky. Enjoy.
28. What’s your favorite sports team?
Always be looking for common ground with this question. If it’s the same team as yours, make a joke about seeing a game together. If her team sucks, make a joke about loyalty being an attractive quality in a woman.
29. Six-pack or dad bod?
Funny question and most women will answer sincerely. Try to use your sense of humor after she answers.
30. What’s the best dinner for date night?
Hopefully, she likes sushi too, otherwise, this won’t work out.
31. What’s your ideal vacation?
Is it a festival, a backpacking trip, or an all-inclusive resort? Here’s another excellent way to learn more about their personality.
32. Red wine or white wine?
After she answers, say something forward like “I’ll make sure to have some ready for after our date”. Not all women like forward, but who cares.
33. What’s your go-to cocktail?
After she answers, ask her if she’s ever been to your favorite cocktail bar. If you don’t have a favorite cocktail bar, get one.
34. Whiskey or Tequila?
You can take this one and run with it.
35. What’s your favorite thing that’s happened this year?
I like this question because it’s real and the answer is usually sincere.
36. Friends or Seinfeld?
If she doesn’t like either, she’s too young for you bro.
37. Favorite sport to watch?
Football is the only correct answer here.
38. Where did you grow up?
And after she answers you can ask why she left.
39. Submissive or Dominant?
This is a not-so-subtle way of creating sexual tension which is ALWAYS a good thing. The super-conservative girls might not go for it, and who cares. Next up.
40. Who was your least favorite teacher in High School?
Join in on roasting her least favorite teacher, and tell a funny story about yours.
41. What’s the most awkward thing that’s ever happened to you on a date?
Awkward usually has a funny backstory.
42. What’s your favorite trend this year?
I hope you’re into TikTok.
43. Who’s your favorite artist this year?
Does she like country, EDM, or rap? Similar music taste is always a good sign.
44. What’s the worst movie you’ve ever seen?
Mine is Cabin Fever. You should watch it.
45. What made you swipe right?
Experiment with this one. It’s aggressive, but if she goes with it then it skips the bullshit and gets right to the point.
46. Pre-game or after-party?
After she answers you can respond, “So pregame at my place before our date. I’ll buy the tequila”. It’s fun and aggressive.
47. What book are you reading right now?
Sappy and boring, but women LOVE to talk about books they’re reading.
48. What’s your favorite city and why?
Strong opener. Hopefully, it’s a place that you’ve been to. Remember, common ground.
49. Truth or dare?
If she’s into it, this can really get the juices flowing.
50. Sushi or Italian?
Get straight to the point. Have a solid dinner spot in the chamber.
Final Thoughts
Remember that not every question should be used to start the conversation.
Use your best judgment and keep your arsenal of good questions large, that way you can always keep things flowing. If you’re ever in doubt, don’t be afraid to be forward and make your intentions clear. When it comes to online dating, there’s really nothing to lose.
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