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Isn’t dating sometimes like a job interview?  You have an open position…seeking “BOYFRIEND” or “HUSBAND”.

Does your guy get the pink slip or a permanent position?


You’ve been conducting interviews for this particular position for quite awhile.

The applicant pool is slim but you occasionally you meet a prospect who “looks good on paper”; meaning his resume meets all the basic qualifications for the “job”.

So you decide to give him a temporary assignment; you start dating. The temporary assignment may evolve into something more permanent but there’s no need to rush things!

It is during this trial period I would recommend you begin to incorporate the bounty of questions discussed in part one and part two of this 4-part series, on questions to ask before getting too serious.

This third installment which focuses on character may be easier to discuss earlier on in the relationship, versus finances (part 1) or past relationships (part 2).

One’s character is comprised of the qualities and traits which make you, uniquely YOU. A boyfriend of poor character should be “fired” immediately.

It doesn’t matter how “good he appears on paper”, if his character is questionable you should RUN!!

I, personally do not believe that a person can change who they inherently are.

As you continue to get to know a new boyfriend, be watchful for signs of who he inherently is.

Unlike the prior installments in this series, his character will become apparent early on in the relationship.

If you are paying attention you will be able to determine whether your guy is of good character…or maybe a bad egg! Everything looks good on the outside, but when you break it open the pungent smell hits you like a ton of bricks.

Like I said….RUN!

Even if you are able to assess his character by observing his daily interactions with you and others, there is still value in having conversations about one’s character so that you can assess whether his words match his behavior. Besides you want to ensure that he is the same in public AND in private, when no one’s watching!


Does your guy get the pink slip or a permanent position?

Here are the fifteen or so questions I suggest you ask to tee up the conversation on character:

  1. Are you inherently generous or stingy…with your time, money, compliments, etc? Does your lady have to “earn” these things or do you give them freely?
  2. Do you ascribe to a religion or faith? Do you practice your faith?
  3. Could you be in a relationship with a girl who is practicing abstinence?
  4. Could you be in a relationship/marriage with a partner who earned considerably more than you or is more successful?
  5. Do you consider yourself a man of your word? What if any circumstances justify you breaking a promise or a commitment?
  6. Do you struggle to admit you are wrong? In a disagreement or argument are you the first to apologize?
  7. What if any vices do you have?
  8. Do you visit pornographic websites? How often? Do you have a sexual fetish?
  9. Were you ever convicted of a crime? What were the circumstances surrounding the incident?
  10. How do you respond to challenging situations?
  11. How long have you been employed by your current employer?
  12. Do you believe in traditional gender roles in relationships/marriage? What are those roles?
  13. How would you respond to your girlfriend if your relationship with a female friend (including an ex), makes your girlfriend uncomfortable?
  14. Would you consider yourself a gentleman? What does that look like in a relationship?
  15. How would you respond if a guy disrespected your girlfriend in your presence; for example, he cut in front of her in the grocery store line or he pushed her aside at the movie theater?

Does your guy get the pink slip or a permanent position.

Character matters, in your relationships, at your job, at school…frankly in all aspects of life!

How is your new guy measuring up?

An assessment of one’s character goes beyond asking whether he’s a good guy!

These questions enable you to dig a little deeper and really decide whether he is who he says he is…and more importantly, does he possess the character traits of someone you want to continue in a relationship with?

Or does he get the pink slip?

Which is it?

I’d love to hear your feedback and feel free to share any character questions I may have missed.

I wish you the best.



  1. I think that these are important questions not only for New daters but for folks in long term relationships. You’ve gotta check in with self.

  2. Married lady here. I like this list of questions! I think these are all valid things that could be asked and investigated before committing to someone. I say investigated, because sometimes people will say what they think you want to hear just to be with you. Sadly, if the relationship isn’t serious you may never get a chance to ask some of these. But time will always reveal the truth and true character.

  3. These are great questions. But I think in addition to asking them, we need to look for evidence. Many people will describe themselves as patient, loving, kind, etc. because they want to be and might truly believe they are–but what do their actions say?

    Someone once told me “love is a verb” and I think that’s so incredibly true. 🙂

  4. Interesting list of questions.The character is very important .you become who you live with .Food for thought.But on a lighter note,I don’t know how honestly I would be able to answer those questions!

  5. This list is everything…I’m married but definitely great advice/tips for singles. I mean, this could honestly save a lot of time for people on the dating scene where character is concerned.

  6. Hmm character very important, but honestly that make take time to really see and understand interesting read.

  7. I suppose that could work whether you are a guy or a girl. My ex certainly had friends that made me feel uncomfortable the way she treated and acted around them. She didn’t care and refused to. But if I had a female friend, she had to denigrate her until she was no longer around. Was bad.

  8. These are the best questions list i have ever seen. A little intense for the average guy hut perfect for me. Maybe if character was placed as a priority we’d have fewer issues. Lovely list again and thanks.

  9. Yes’ I think to myself all the time that the whole getting to know phase is like a job interview. And you have got to ask the right damn questions and keep questioning the other person constantly!
    Great post

  10. My favorite: “Could you be in a relationship with a girl who is practicing abstinence?” This is very important. I dated a guy, briefly, who admittedly said that he couldn’t do it. I was so proud of myself for asking but even happier that he gave the answer I deserved to make the right choice.

  11. Your advice in this article is on point! Character is extremely important in a relationship, especially if you’re looking for it to last long term. The questions that you posed will definitely help someone discover more about the other person. Thanks!

  12. Have you ever cheated in a relationship? What was the reason for you step outside of the relationship?
    Would you consider having or have you ever had sex with the opposite sex?

    1. Great questions Mary! I considered including those questions in this list, however, I already had them on the 15+ Questions to ask about Past Relationships post, so I didn’t want to duplicate. Those three are so important!

  13. I love this blog post… we as women find it hard to ask the serious questions until its too late. In my opinion… its really about self-love… if you love self… you want the best for yourself and that will allow us to ask those 15 questions that you presented! Stay blessed Queen and thanks for sharing!

  14. lol, this is funny! i will have my husband read this. I agree with you. Nobody can change somebody’s character.. but their own selves. And it is tough to do it. Im just glad that I got a good catch! 🙂 Thank you for sharing this!

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