12 Questions You MUST Ask Him If You're Dating After 40

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12 Questions You MUST Ask Him If You're Dating After 40

To tell if he's a keeper or not.

A lot of people feel like dating in your 40s is like being in hell. I have to say that I disagree.

Sure, there are advantages to dating when you are younger, but when you're in your 40s, you don’t have the pressure you did when you were younger.

Most likely, you are more financially secure and in a career you like. You either have children or have given up on the idea of children. And, you aren’t in a rush. This is the time where you can really enjoy dating.

You also have a much better idea of what you want in a relationship, what you will put up with, and what you won’t.

As human beings, we need to connect. If you feel this way, then you are normal. Remember, it’s alright to say no and to wait for something better to come along.


Here are 12 questions to tell if he is a keeper or not.

  1. Why are you single?
  2. What is your biggest insecurity?
  3. Are you looking for something serious or casual?
  4. Are you thinking about making any major residential moves in the next year?
  5. Have you ever struggled with any mental health issues?

  6. Have you ever been arrested?
  7. Have you ever been in a serious relationship before?
  8. What memories have scarred you for life?
  9. Are you close with your family?
  10. Do you call your mother without prompting?
  11. Tell me everything about your drinking or drug habits.
  12. How do you think this is going so far?

Dating after 40 doesn’t have to feel like hell. Some of these questions may be hard to ask, but they are well worth it. You can also add more of your own.

Remember that you're trying to make a good first impression. This shows that you are genuinely interested in your date. Nobody likes it when they go out on a date and don’t feel like they could get a word in.

It’s also important to be honest with your date and yourself, about what you are looking for. I find there is a venue for everyone these days, so, there is no reason to lie or take advantage of others. If you have kids, let your date know.

Don’t try to hide yourself from your date. You are a really fabulous person, inside and out. There is someone out there right now, dying to meet someone like you.

Lianne Avila is a Licensed Marriage & Family Therapist is San Mateo, CA. She is genuinely interested in helping you thrive in your relationship. For more information, please visit Lessons for Love.

This article was originally published at www.LessonsforLove.com. Reprinted with permission from the author.