Bold First Date Questions That NEED To Be Asked

bold first date questions

First dates. We’ve all gone on a few.  They can be something out of a romantic comedy or something out of a cheesy horror film.  One thing I’ve learned from working with coaching clients is that many times deception and lies start from the very first date!

Here are some deep first date questions that absolutely must be asked.  By asking these (sometimes uncomfortable) questions, you will avoid stress and drama in any budding intimate relationship.  Also if you don’t feel quite ready to ask these possibly awkward first date questions, you will see the value in deciding to hire a dating coach.

Asking first date questions that are a bit bold will save you time, energy, and possible heartache later! Click To Tweet

First Date Question #1: Ask about other current relationships

first date questions relationshipsFirst things first.  Any person going out with someone new for the first time probably has limited knowledge.  Especially of that person’s relationship history.  Here are some deep first date questions that should be asked to ensure full disclosure.  Ask if the person is:

  • married,
  • engaged,
  • dating (casually or serious),
  • in  a “friends with benefits” situation,
  • has a crazy ex,
  • shares parental responsibilities with someone else

I have countless clients who have ended up with broken hearts because they assumed the person they were dating was single.

Don’t assume!  Ask point blank.

I have found that’s it’s much harder for most people to lie directly to someone’s face.  This means “players” will be found out quickly.   A lot of heartache and time will be saved by understanding the other person’s relationship status upfront.

First Date Question #2: Ask about sexual orientation

first date questions- sexual orientationToday people are more open, honest, exploratory and fluid in their sexuality.  This means that it’s very important to know the sexual orientation of a potential intimate partner.  When I coach on this with clients, they are skeptical of asking awkward first date questions such as this.  This means my goal when a client decides to hire a dating coach is to ensure that they understand the “why” behind the question.

I tell them that the goal of this question is to ensure total comfort and acceptance of the sexual orientation of the person they’re dating.  If this bold question is asked on the first date, it will avoid any surprises in the future.

First Date Question #3: Ask about thoughts on exclusivity in intimate relationships

This is an optional first date question.  Some people aren’t concerned about monogamy in their intimate relationships.  If that is the case with you, then skip this question.  However, for my clients who do want exclusivity and monogamy in their intimate relationships, this is something that should be discussed on the first date.  The more informed a person is upfront, the better decisions they can make.

I know, I know, these questions may seem a little silly, blunt or scary to ask on the first date.  However, they don’t need to be asked like a person doing a job interview!  Each of these questions can easily be added into casual dating conversation without digging too deeply.


Dating is hard enough.  Asking the right first date question can:

  • prevent misunderstands
  • address false expectations
  • help you to better understand the person you’re pursuing an intimate relationship with

and most importantly…save you a TON of time, energy, and emotion.  Anyone who wants to build their confidence and comfort with asking such questions would greatly benefit from the decision to hire a dating coach.  Don’t put love on hold any longer, book today!

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Other blog posts of interest:

How Are You Finding Your Bliss?
Importance of Sex in A Relationship
7 Reasons Women Are NOT Calling You Back (For Men Only)
7 Signs That Intimate Relationships Aren’t Your Cup Of Tea
Dating Around: Controversial Reasons Why He is NOT Calling You Back! (For Women Only)