Questions to Ask on Third Date


posted by on Relationships


Wow, so you are on date number three and you like the guy, at least enough to continue seeing him, plus he is a man of his word and you like the dependability. It’s time to get to know this guy on a deeper level and if you have been dating for fun, is it possible that in the past two dates you have not learned this information.

Here are my top questions to find out after a third date. 

1 How long is a reasonable time before you think you know if you’ve met “the One”?

If it’s over 2 years, RUN! It doesn’t take that long to know if you want to be with someone forever. For those of you with the goal of marriage you want to know how long until you can get engaged.

2 If you were to corner his ex what would be the reason she said they broke up?

We know that most of this story will be bullcrap, but you are looking for how he speaks about his ex, is he respectful or not. You aren’t concerned about the story as much as you are about the tone of the story. Danger signs: anger, hostility, bad mouthing, name calling, whining.

3 If he is over 35 in the cities and 30 in rural areas, why hasn’t he gotten married?

This answer might be crap to but look out for if he actually wants to be married, if that is your goal.

4 What is your career path and if it doesn’t work out then what?

Let’s see how ambitious he is, and if he is open to change. If he is hellbent on being a rapper, he might not be the person for you.

Also watch for how you two communicate when you disagree, can you talk it out or is someone being passive aggressive? Pay attention to it all, disagreements is not a sign of a bad relationship its means you have different opinions, but if someone makes the other person wrong then there is a problem.

You have earned the right to ask a few more questions and make sure to watch his body language. If at all possible, avoid sleeping with someone before you really know them, it messes up the process and makes you less objective.


To avoid the interrogation tone, make sure to be kind, smile and avoid making harsh comments, it makes others not want to share. You want him to feel safe. Also from woman to woman, avoid siding with him in regards to his. Remember there are two sides to each story.



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