8 Questions To Ask A Guy To See If He’s Worth Dating

You have to get in the habit of thoroughly screening potentials before you get too attached. A lot of toxic guys show their red flags right away and bank on finding a good woman who will fall for their tricks to take complete advantage of. You don’t want to set yourself up for heartbreak by not properly weeding through crappy matches. Here are 8 solid questions you need to ask a guy when you’re trying to determine if it’s safe to proceed into dating waters with him.

  1. What happened to your last relationship? Also under this is- why did your longest lasting relationship end? Bringing up the dreaded ex-talk can be so uncomfortable, especially if you don’t want the tables turned on you to bring up your baggage, but a lot of times it is less about “her” and that particular connection and more about revealing his thought process toward women in general. Guys who are full of themselves will gloss over stories of how they were completely wrong in a scenario as a valid reason to break it off with someone. Or they will uncover how petty and careless toward respecting females they are when they share how they’ve handled the breakup and after. It also is telling about their maturity level if all they do is put blame on the woman and fail to mention any of their shortcomings or faults that contributed to the relationship failing.
  2. What is your 5-year-plan? It’s important to match energy with someone. You don’t want to be a go-getter and find yourself compensating for a progress snail. It will drain all your resources and cause you to lose respect for that person. It can also give you an idea of where you could fit into that person’s life. If they talk about running around the world traveling and living carefree, but you have your mind set on planting roots and raising a family, you two may not be on the same page if you choose to move forward together.
  3. Did you go to/graduate college? This may be debatable, but in my opinion, a big variance in education level is noticeable. Even at the workplace, I can detect a significant difference in the amount of gossiping and lack of focus on work ethic when I’m surrounded by opposing levels of higher educational achievement. For me, it just doesn’t work for opposites to succeed when it comes to this and you should be mindful upfront about a potential clash of mentalities.
  4. What was/is your relationship like with your parents? No one has control over the family they were born into, so I wouldn’t use this as something to hold against someone if there isn’t a positive history there. But what they have to say about their childhood and how they’ve continued to keep in touch with their family can reveal how they take responsibility, how they handle conflict, and whether they’re still too wounded to be ready for a healthy relationship. You don’t want to fall into the trap of feeling too sorry for someone who had a difficult upbringing that you end up taking them on as a project to “fix” or “save” them instead of entering a mutually considering partnership. Regardless of where we came from, people should be responsible for their healing at some point and not feel entitled to dump their wounds on a potential significant other.
  5. Do you want any/more children? This is something you want to know right away. It would totally suck to get attached to someone and not be able to imagine a future without them only to find out after the fact that your views on children don’t match up and neither of you is willing to budge on it. If your answer to this question is a deal-breaker, better to find out sooner rather than later.
  6. What are you looking for relationship-wise and do you have a timeline? If you’re looking for a relationship with a clear title moving forward in the typical progression, this is something you need to ask directly. Any response that is ambiguous or inconsistent should be immediately left alone. You don’t want to waste your time in an endless situationship when he knew from the start he never wanted anything serious. You also want to weed out a user if he seems like he’s pushy about moving things forward too quickly, because he may have ulterior motives for his pursuit.
  7. Would you be willing to introduce yourself to my dad/parents/close friend? This may seem like a bit much and antiquated, but transparency is necessary these days for safety purposes. Toxic people know to isolate their victims, so the sooner you make it apparent other people are invested in protecting you and he will have to answer to them, the faster you’ll weed out someone who is a fraud or potentially dangerous. If he’s serious about respecting your worth, he shouldn’t mind going through the proper steps to get to know you better and spend time with you. You also want to make sure the guy he is when it’s just you two behind closed doors matches who is he to others, especially if he’s being dishonest or wearing a mask.
  8. What interests you about me? If the first one to three things that come out of his mouth are physical attributes, leave him alone. Sure, it’s nice and all if he notices your pretty eyes, but he should want to be with you for more substantial reasons than your looks. Also, if he’s too focused on the physical that’s probably all he wants a part of as well.
I’m Cara, not to be confused with Carrie, although you could say I’m a Millennial Bradshaw of sorts. Pop culture connoisseur. Lover of all things creative and passionate about health and personal well-being. Follow me on IG @cara_vale_writer