Dating can feel like a chore, especially if you invest too much time getting to know the wrong person. Asking the right questions at the start can save you days, weeks—even months—dating the wrong man.
One of my clients, a successful woman in her mid-fifties, asked, “Rhonda, I waste so much time dating men before I discover something that’s a deal breaker.”
We get so caught up in the first connection, passion and newness of meeting what seems like a great guy, that we forget to ask intelligent questions.
Having the same challenge as Shelley?
Some of these questions may be important to you—others not so much. Think about what’s TRULY important to you and craft intelligent questions to ask.
Several well-thought out questions can reveal answers and insight most women only discover after a month (or more) of dates.
Questions to Ask Him by Email, Phone or in Person:
How often do you visit or see family (parents or children)?
Many couples have arguments—especially during the holidays—due to one partner wanting to spend time with family. If he is divorced and has children, this is very important to know before you go further.
You can’t just assume how things will go. It’s something you should discuss before either of you commit.
Also, some mature daters are also taking care of parents—physically and financially. You both need to know what each others responsibilities are before moving forward. Can you handle them?
This question can also uncover the quality of his relationships with his family. For some, having good relationships with family is a must.
What do you love most about your work?
I knew a guy who seemed to have a wonderful work. After a couple conversations, it turns out he wasn’t happy with his contracts. He was in the middle of mediation and it looked like he was going to take them to court.
Someone who’s in the middle of work-related conflict isn’t going to have much bandwidth for you. It’s best to let them get settled before starting something.
What are you looking for in a relationship?
Never assume because you read his profile that you know what he wants. Just ask.
If you think it’s too bold. It isn’t. Marriage-minded men have asked me this point blank—on the phone and on first dates. You’re both on a date for a reason.
How is your relationship with your ex-wife?
Years a go, I was on a date with a dreamy Swedish businessman. I asked him this question and it all came out. They had a nasty relationship. I could foresee it flowing into any relationship he went into.
There’s nothing wrong with dating a divorcee—you just don’t want to be in the middle of any drama. I’ve dated men who have great—or at least civil—relationships with the ex.
Are you open moving?
I went out with a man who had a 7-year-old girl. I asked him this question. He said he wasn’t open to moving from her school district until she was 18. With so many children growing up away from their fathers, I respected him for making that decision.
Yet knowing international living and travel are an integral part of my lifestyle, I knew it wouldn’t work.
Better to find out before investing your heart.
This isn’t about bashing men for wanting what they want. It’s about freeing him to be with the right woman for him.
You’re doing him (and yourself) a big favor.
Click “Share” on Facebook and save your girlfriends from wasting time with incompatible men.
With love and in service,
P.S. Ready to attract and date the right, high-caliber man? Ready to show up fully as a high value woman? Visit my bio for your free gift “4 Ways to Instantly Show You’re a High Value Woman.”