When you start dating someone new, you’re probably a bit restrained at first because you don’t want him to think you’re “crazy” or too needy, but that’s complete BS. If you’re looking to build a meaningful relationship, why shouldn’t you be upfront about who you are right from the beginning, and why shouldn’t you expect him to do the same? After all, the last thing you want to do is waste time with someone you’re not compatible with. With that in mind, don’t be afraid to ask him these questions so you can know what you’re getting into from the start.
What are your ultimate career/life goals?
It’s great to meet someone you enjoy having dinner and seeing movies with, but the point of dating is to find someone you could spend forever with. Strong, independent women don’t want to spend forever with someone who’s unmotivated or indifferent about their own success. If a guy is unable to articulate his goals into words, it means he’s not serious about his future, which means you can’t be serious about a future with him.
Do you want marriage and/or kids? If so, how many kids?
Everyone has a different definition of an ideal family, and it may or may not include marriage/kids. The important thing is that you’re both on the same page, and you deserve to know where he stands before getting too involved with a guy. If you want kids and he doesn’t (or vice versa) you should have the opportunity to move on quickly and find someone who wants the same things you do.
Do you enjoy your current job, and could you help support a family with it?
Both parts of this question are important, because no strong woman wants to be with a guy who’s underemployed and constantly complains about how much he hates his job. Especially if you want kids, you deserve to know whether he’s capable of raking in enough dough to chip in for expenses such as formula, diapers, car seats, and day care. You don’t want to find yourself financially supporting both your child and your underemployed partner.
Are you still in contact with any exes and do you still have feelings for them?
Guys who are still hung up on an ex are the worst kind of project, and you deserve to know if you’re getting into that kind of situation. When you’re being brave enough to put yourself out there and trust someone new, you deserve to know what’s in his heart and if there’s any room in there for you. If not, you deserve the truth so that you can move on.
Are you religious or spiritual? If so, what are your beliefs?
Religion and spirituality are highly divisive factors, and they generally require some kind of agreement (or sometimes an agreement to disagree). There’s nothing wrong with wanting your partner to share your faith (or lack of it), so you shouldn’t be afraid to verify whether or not you’re compatible with him in such a crucial way.
What’s your relationship with your family like?
Overall, you can learn a lot about someone by how he interacts with his family. Dating is about finding someone to start a new family with, and the best indicator of the future is usually the past. He may have had some issues with his family in the past, but if he’s managed to maintain some kind of relationship with them despite the hardships, he’s probably serious enough to consider starting a new family with.
What’s your credit like and how much debt do you have?
There’s a difference between a financially responsible woman and a gold digger. Strong independent women don’t insist that a guy have stacks of cash in order to win our love, but we do want a guy whose financial situation is reasonable enough to be able to accomplish life goals such as buying a house in the future and sending our potential future children to college.
How many sexual partners have you had?
It’s such a taboo thing to ask, but we deserve to know if we’re attaching ourselves to a former or current Barney Stinson-type (and his list of 200+ random one-night stands). It’s more than a matter of honesty; it’s a health concern, as well. You won’t judge him for having a double digit number, and he shouldn’t judge you either, but you’d be just a bit concerned if he’s up in the triple digits and haven’t been tested in a while.
Do you have any unusual sexual fetishes?
No one can think of a good way to ask this question, but everyone wants to know. Most people are comfortable experimenting with a certain level of mild kink, but some fetishes require both parties to be fully comfortable. It’s not a big deal if he likes high heels, handcuffs, and spanking, as those are all fairly normal, but a heads up would be nice if he prefers something a bit more unorthodox to get his juices flowing.
What annoys you/makes you angry, and how do you express your anger?
When a relationship becomes serious, anger can become a big problem. You deserve to know if you’ve bonded with a hothead who may become verbally or emotionally abusive in the future. Abuse is never okay in any form, so the sooner we can find out about these issues, the better.
The bottom line is that you should be allowed to ask the important questions when you’re considering an arrangement that could last forever. If someone is so indoctrinated by this world of shallow casual “dating” that they would actually be offended by such important and real questions, there’s a good chance that they’re not right for any strong independent women. It’s a good thing to be picky and decisive, so don’t sell yourself short when it comes to forever.
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