Nerves get the best of us when it comes to going on a date. We overthink, try too hard, or fall into surface-level conversations because of the daunting idea of getting deep. What if I told you that getting deep with him on the first date makes a lasting impression? I’ve got some confidence-boosting advice for you before you go on your next night out. Read my curated tips below. 

Editor’s note: Although this article uses male pronouns, the advice applies to all sexual orientations and gender identities.

Ask These Questions to Make Him Think About It/You Later

There is a questionnaire that you can use that will significantly increase the chances that he’ll fall in love with you. Arthur Aron, a psychologist, used the 36 questions below in his study to make two people fall in love with each other. Sounds unconventional, right? I thought so too until I found out that these same questions by Aron were used in hundreds of different studies and worked.

Set I

1. Given the choice of anyone in the world, whom would you want as a dinner guest?

2. Would you like to be famous? In what way?

3. Before making a telephone call, do you ever rehearse what you are going to say? Why?

4. What would constitute a “perfect” day for you?

5. When did you last sing to yourself? To someone else?

6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?

7. Do you have a secret hunch about how you will die?

8. Name three things you and your partner appear to have in common.

9. For what in your life do you feel most grateful?

10. If you could change anything about the way you were raised, what would it be?

11. Take four minutes and tell your partner your life story in as much detail as possible.

12. If you could wake up tomorrow having gained any one quality or ability, what would it be?

Set II

13. If a crystal ball could tell you the truth about yourself, your life, the future, or anything else, what would you want to know?

14. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?

15. What is the greatest accomplishment of your life?

16. What do you value most in a friendship?

17. What is your most treasured memory?

18. What is your most terrible memory?

19. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?

20. What does friendship mean to you?

21. What roles do love and affection play in your life?

22. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.

23. How close and warm is your family? Do you feel your childhood was happier than most other people’s?

24. How do you feel about your relationship with your mother?



25. Make three true “we” statements each. For instance, “We are both in this room feeling … “

26. Complete this sentence: “I wish I had someone with whom I could share … “

27. If you were going to become a close friend with your partner, please share what would be important for him or her to know.

28. Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.

29. Share with your partner an embarrassing moment in your life.

30. When did you last cry in front of another person? By yourself?

31. Tell your partner something that you like about them already.

32. What, if anything, is too serious to be joked about?

33. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?

34. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?

35. Of all the people in your family, whose death would you find most disturbing? Why?

36. Share a personal problem and ask your partner’s advice on how he or she might handle it. Also, ask your partner to reflect on how you seem to be feeling about the problem you have chosen.

Avoid Saying These Words

You don’t have to analyze every word before you say it, but to avoid sounding insecure. Steer clear from saying:

Maybe …

A little …

I think so …

Remember shyness is cute. Uncertainty is far from attractive. Oh, and don’t say “literally…”

Be Decisive

When you’re on a date the other person will notice the little things. By no means am I saying hide who you are, but for goodness sake don’t take 23 minutes deciding what to eat on the menu. 

Give Him a Compliment

Men, as much as the next person, enjoy a compliment here and there too.

Leave a Little Mystery

Be vague with some answers to your questions. Don’t tell him every little detail; it’ll keep him wondering or wanting to know more.


Leave Your Appearance As-Is, Once You’re on The Date

Leaving your date at the table while you go to the restroom to fix your makeup is perhaps customary for most women. Yes, taking your time to get ready and looking good on your date is always praised by men, but interrupting the flow of your Date to double-check your appearance is unnecessary. Don’t worry, you still look great honey.

Make Eye Contact

We have all been guilty of lacking some eye contact when we’re nervous. Take a moment to hype yourself up (in your mind) before you look him straight in the eyes. Trust me, if there’s a connection, you’ll feel it. 

Change How You View “The One”

When you let go of the false perspective that the next guy you go on a date is “the one,” you are also letting go of any expectations that you may have had for him. Leave no room for disappointment. Change your narrative. View the date as something as simple as getting to know someone new. 

Show Up As Yourself

It’s exhausting to try and be a person that you think might seem more attractive. Your date wants to get to know you, so stop trying to figure out what they “want.” Don’t force something that isn’t there. It’s okay if you’re not a match.

Make It Apparent That You Don’t Need Him, You Want Him

Change the need into a want. Again, perspective. How do you feel when someone shows you they are always available, versus someone who makes time for you in their schedule? 

If He Pays, Thank Him for Dinner

Having manners is always important, and he will tell his friends about the girl who did not say “thank you.” Don’t be her. 

Permit Yourself to End The Date


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