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7 Awkward Questions You Must Ask on a First Date – And 3 You Really Shouldn’t


7 Awkward Questions You Must Ask on a First Date – And 3 You Really Shouldn’t

Bonus: 3 more questions that you shouldn’t ask on a first date.

If relationships are compared to a video game, then the first date is like the last and most dangerous gang boss you face. The first date is one of the trickiest of all social situations and many people, depending on how much they like their date, spend sleepless, anxious nights thinking about them. And worse, first dates are different for all people. There’s no clear-cut magic formula for them.

So what is the secret to a good and positive first date?

Well, both parties’ should put their cards on the table.

A first date that isn’t honest is not a proper one. You aren’t setting a good example for the rest of the relationship if you do it that way. In many cases, you might just be foreclosing the possibilities of having a relationship in the first place.

So to help your cause and to kick-start you towards a meaningful relationship (assuming you want one), here are 7 must-ask first-date questions:

1. What exactly are your expectations from a relationship that might result from this?

This is as candid as it gets. Asking this makes you come out as the honest and undeceiving individual that you would want to be.  Also, depending on the answer, you two would know if it’s simply a mutual waste of time or not. A lot of pain and possible heartbreak avoided in one fell swoop.

2. Do I meet your expectations?

Online dating, which is like the most prevalent of dating nowadays, is deceptive. We all know the miracles a good camera angle and a good camera in general can bring about. So asking this makes things clear. This saves a lot of pain later, along with a lot of dissatisfaction and dissent later. Also, both parties should be sensible to take dating profiles with a pinch of salt.

3. What’s something you think I should know about you, if we were to date?

This can be anything from an addictive behavior to sexual preferences. Anything that helps you gauge each other’s compatibility is a win-win. The key trick is to get each other in a space, consciously and subliminally where the deepest of things, the most fundamental of choices and preferences, good or bad, come out. This would not cause/save you two a lot of awkward conversations later on in the advanced stages of the relationship.

4. What might constitute a deal-breaker for you?

This is the ideological apparatus coming into play in the relationship. This is especially pertinent for people who stand with strong opinions. Remember Elaine from Seinfeld who wouldn’t date a dude because he wasn’t pro-choice? That’s what we are talking about. Another kind of people this should be important for, are the ones who are dating people from other disciplines/areas of expertise. If a literature major dates an engineer, there is a high chance that someday some argument might blow out of proportion.

5. Are you okay with this?

This is the part where you talk about your preferences and addictive behaviors or questionable living habits. This is the corresponding point to #3 for you. When both parties clear things out before getting into a serious commitment, it’s better for both of them.

6. (After it’s done) So do we have a possibility of a second date?

Very important question but most people chicken out when asking it or they just simply defer it indefinitely aka ghosting. This question, however it is answered, either forecloses any chances of being hopeful or gives rise to meaningful hope, hope that might just see fulfillment.

Must-Read: Men Are from Mars, Women Are from Venus: The Classic Guide to Understanding the Opposite Sex

7. When was the last time you got tested?

Not the first question, but definitely once you two have delved into sex-related things at length. This is important as people get reckless at times when it comes to using protection during sex. And given how free and common the activity is – the way it should be, people should get themselves tested frequently.

Bonus: Three Questions You Shouldn’t Ask on Your First Date

1. How is someone as hot as you still alone?

Just no. Besides the obvious cliché, it shows you are insecure about yourself and think that despite the person being obviously interested in you, is too good to be with you.

2. General questions about marriage/future/kids

No. Too fast. Too early.

3. How much do you earn?

Too fast. Too early. You’ll just end up coming out as cheap. Or that you are only interested in money.

Must Read The Best Books about Love and Relationship:

  1. The 5 Love Languages: The Secret to Love that Lasts
  2. The Seven Principles for Making Marriage Work: A Practical Guide from the Country’s Foremost Relationship Expert
  3. Men Are from Mars, Women Are from Venus: The Classic Guide to Understanding the Opposite Sex

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