First Date Questions.


It’s another weekend, another chance for people to vent out either how terrible or good their week has been or another opportunity to get randomly social.  One thing’s for sure a couple of you might be heading for a first date somewhere. Dating is such a complex arena considering the versatility of social media and dating apps. Well, I haven’t been on a first date in  about four years, but if I was, there are some questions I wouldn’t miss out on asking. These might sound corny or crazy or just realistic, but for an over-analyzing person like me, they are necessary. I realized the older we grow, the lesser looks and physique really matter, so why not establish these grounds before getting too wrapped to let go.

Stone Artwork

  1. Do you have a Family?

Well, ladies and gentlemen, it is vital to establish whether the person you’re on the date with is actually single? Is he or she married? Do they have kids? If the answer is along the ‘It’s complicated’ line well, I’m out. There’s nothing worse than dating someone with issues because, in the long run, you’ll end up much more emotionally twisted than they are. Additionally, I do not condone cheating or worse cheating on your partner with me.

  1. Do you have a criminal record?

Yes, I want to know if I am dealing with a thief, a violent person and so on. As I mentioned before, I am crazy, crazy enough to look out for myself. We have all heard of Tinder dates go wrong, and girls – especially, ending up abused or missing. Just to be safe run an online search of the person – that’s if you didn’t know them earlier, there are plenty of sites online that can give you pretty much all the information you need on someone.

adult, beverage, black coffee

  1. Where do you work?

This is my casual way of asking; are you broke? Nobody wants baggage. Ladies are out here being gold-diggers, and some men can’t afford to pay for a decent meal. Fact is after all the lovey-dovey, bills need to be paid, and girls want to have some fun. For the guys, don’t bite more than you can chew; you can tell if a woman is there for your wallet, the amazing food or you. For the ladies; this does not translate to ‘I can’t date a broke man’.  However, if the man doesn’t have any ambition, vision or aspiration to change this, that’s a red light. Period.

  1. What’s your relationship with your parents?

Okay, I know this might be a little intrusive, but that’s why we’re on the date in the first place. This question helps me evaluate the mental health of the person I am dealing with. You can tell a lot about a guy from the way he talks or relates to his mother. On the other hand, some ladies with daddy issues tend to have some emotional constraints that might just creep into the relationship, later on.

Two Stainless Steel Padlocks

  1. Where do you see yourself in 5 years?

I love a man with a plan, I love a man with a dream, and nothing triggers me like a man with ambition! If your date doesn’t know where they will be in 5 years, how do you expect them to know where they see themselves with you? The fact that you two are on a date shows there’s a level of interest in each other, in the event whereby this interest grows and blossoms into a relationship you have to be sure about it from the get-go.

Millennial dating is insane, but somehow we get through it. Whether you’re hooking up for some fun or searching for a lifetime commitment, it is necessary to get to know the person. We’re past asking favorite colors, likes, and dislikes. People treat you exactly how you portray yourself. First impressions matter, so do first dates! For couples, it’s also cool to reinvent these first dates once in a while.  Lovely weekend guys; be authentic, be you!

Silhouette of Man and Woman Kissing



20 thoughts on “First Date Questions.

  1. Nice one Anita. And yes we are past asking about fav colors, food etc. I love the last question. It really counts knowing if you are about to date an ambitious person or not.

  2. I love this. Especially the family que. Most families in the current age are really broken…if she comes from an abusive home for example she might probable assume that one time you are going to hit her…or if her father is a drunk….point is…her view of a family is twisted and narrow. …..with this que you get to know how best to treat your woman..
    The criminal record?? hehe i do not know what to say about that.
    Awesome stuufffff

    1. I gave a disclaimer, lol. I’m crazy! But it is very important for one to know what they’re heading into, better safe than sorry.

  3. Great stuff Anita! these are definitely first date questions. the longer we put off asking them, the tougher and more awkward it gets to have such conversations

  4. Nice piece even tho i barely hold the thot…… i also need to know if u av a kid that u dint want or ua family thinks u r the black sheep, n above all if u ask me about the 5 year plan du u also have one….i gues its all both ways ask me white i want black but u also have an answer of why u hate black or otherwise…

  5. Criminal record!!! he better come with his recent certificate of good conduct, no one can admit being a criminal( thief) hihiii
    Its a nice piece

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