Online Dating: How Do You Ask Potentially Awkward Questions?

Online Dating: How Do You Ask Potentially Awkward Questions?

After being matched on a dating app, you had a good number of great conversations with this guy until they culminated in a first date.

A first date led to more.

Everything has been transpiring splendidly, from conversations you have had with him in-between dates, to the dates themselves.

Unfortunately, in the midst of these good dates and conversations, he recently told you something that has led you to suspect that there is a deal-breaker afoot.

This suspicion has made all the good vibes you have been having with this guy so far come to a screeching halt.

This is a potentially awkward question that means a lot to you.

Knowing the definitive answer to this potentially awkward question is pivotal, given that it is a deal-breaker that would keep you from wanting to pursue a relationship with this guy.

It’s normal for people to have a variety of deal-breakers when seeking out a partner.

Popular deal-breakers such as not wanting a match who is unemployed, homeless, married, a criminal or a smoker.

Everyone has a right to have deal-breakers, and many of the popular deal-breakers are justifiable.

This being said, it does feel awkward to come right out and ask a guy whether he is unemployed, homeless, married, a criminal or a smoker.

These are potentially awkward questions no matter how legitimate they are.

Given that you have already built some good rapport with this match and gone on a few dates with him, you remain uncomfortable with the idea of asking him questions in this vain.

This far in, you have enjoyed your time with him and do worry about ruining what you have built with him.

Notwithstanding, these are questions that you know have to be answered to determine whether you are talking to a guy who has long-term relationship potential.

Regardless of how awkward you are about asking these questions, they need to be asked.

You know this.

You don’t want to put yourself in a situation where you spend the next several weeks and months talking and going out on dates with this guy, only to get your answer and have to end it.

This would be a mutual waste of time and effort.

Ergo, you must know now.

Take solace in knowing that this isn’t as awkward as you think it is, when you do it right.

Introduce the topic by using yourself as an example.

Let’s say that you have a strong suspicion that your match still lives with his parents and this is a deal-breaker to you.

There was something he said in a past conversation that made it seem like he lives with his parents.

You know that you don’t want to be with a partner who lives with his parents.

After all, you haven’t lived with your parents since you were legally an adult at 18, and would want to match with a guy who is independent too.

In this scenario, introduce this topic by starting with a story that connects to your own living situation.

Tell him a funny story about the new neighbors who recently moved in next to or across from your home or apartment, one of whom seems to like walking around naked in his living room at night.

By making your story humorous, you make it personable and fun to listen to.

This way, when you segue to asking him about what his neighbors are like and whether he has a crazy story to tell about them, it feels very natural and unrehearsed.

In using this strategy, you have redirected the topic of living situations to him.

You didn’t come right out and directly ask him whether he lives with his parents, but in enquiring about his neighbors, you have made it so much easier to follow up on his answer by asking him about who he lives with.

This is how you confirm whether your suspicion about his living situation is accurate, without making the delivery of the question sound awkward.

Do this with any future match you have.

Whenever you have a potentially awkward question to ask a match, use yourself as an avenue to get to that topic.

Tell a funny or interesting anecdote around the topic through using your personal history, then throw the topic back at your match in the form of a direct or indirect question in reference to what you want to learn about.