Best Online Dating Tip – Don’t Play 100 Questions

Do you know anyone who loves going on job interviews?  Ya, neither do I.  But apparently, the 100-questions interview-routine is still alive and well in the world of dating.  If you are that person who insists on treating the dating process like a job interview, please keep reading.


First and foremost, dating should be fun, from the beginning to the end!  People get nervous, I get that. I used to get very nervous before, during, and after a date.  I would even get nervous just talking to them on the phone.  My palms would sweat, my heart would race, and I would get dry mouth.  Ever have a conversation with someone when you had dry mouth?  It’s not cute, or fun. No wonder I hated that step in the dating process, I was so focused on trying not to sound like I had a speech problem, that I couldn’t even be myself during the conversation.

Crazy, right? So, how did I get over my nervous dating jitters?  It was a long process.  I had figure out what was making my nerves go into overdrive and I knew that until I realized what my problem was, I wasn’t going to be able to change.

It took a lot of introspection, but I did end up discovering that I was my own worst enemy.  Why was this so?  Because I allowed my own insecurities to swirl non-stop in my head.  “What happens if he doesn’t like me?” and “What happens if I say the wrong thing?”  became my two best friends.   I was a professional What If’er.  I was also exhausted and stressed out.  In the end, I realized that it wasn’t the dating that stressed me out, it was my own thoughts.

So, I decided to make a drastic change.

Oh, it was hard at first.  I had arguments with myself.   I swore a lot.  I even found myself mumbling things out-loud like a crazy person, but I was determined to rid that useless negativity out of my head.  Eventually, I took control over what I allowed into my thoughts, and just like a muscle, the more I used my self-control, the stronger I became at kicking anything negative, to the curb.

I also didn’t project, and ditched any expectations I might have had about my date.  Was it hard?  Hell, yes it was!  And during those times, I narrowed down my thoughts to the things that brought me joy, like deciding what I was going to wear on my date, and what yummy cocktail I was going to order.

Easy for me to say, right?  But it can be easy for you, too.  Think of dating as if you are going to a cocktail party.  Think about the fun you’ll have and the great outfit you’ll wear.  Who doesn’t like dressing up?  Never been to a cocktail party?  Then think of it like you are going to a friend’s BBQ.  There’s no reason to get nervous about that, right? Everyone has fun at a BBQ, because that’s why you are there.  To. Have. Fun.

It’s the same concept with dating.

When you focus on having fun, you ditch desperate measures, like using the 100-question routine.  People who bombard the other person with questions during the get-to-know-you process, do that because they think that keeping you on the defense is going to give them the upper hand.  Why do the need the upper hand?  Clearly, they have insecurity and they really have no business dating.

My gorgeous, best-friend Mary, recently met one of those 100-Question people.  They had met on and during the get-to-know-you process, he used the 100-question routine with her.  Here is our texting conversation on how that worked out for him:

CARRIE:  Enough about my crazy life, I’m being rude.  I didn’t even ask you how your phone conversation went with the guy from Match from Hell.

MARY:  Convo with him was okay.  He was Mr. 100 Questions.  He’s a teacher, so he wouldn’t let up.  Every time I just gave a casual answer, he wanted to dig deeper.  I even told him at one point, I thought he was being a little too inquisitive and he apologized, and said it’s the teacher in him.  Needless to say, the questions led to the truth of the matter. I kept it as a positive outlook, but…we will see if I hear from him again. It was just another talk that felt like an interview.

CARRIE:  If it felt like an interview, why didn’t you just tell him?  Jesus, was he reading off a checklist?  What is wrong with people?

MARY:   That’s totally how it felt.  His last question was, “If I choose to go out with you, will you be able to make time for me?”

CARRIE:  That guy needs me.   He needs me to slap him upside the head with some of my advice!

MARY:   Why are you still single?

Do you want a relationship?

Why don’t you have kids?

Would you still have kids?

Why haven’t you been dating?

What changed in your world that you haven’t been dating?

Why have your priorities changed?

Those were all the ones I was skirting around trying not to say “I was diagnosed with MS.”  Finally, I just said it.  I couldn’t take that game any longer.  He does need you! Haha!

CARRIE:  Oh, he did not!  Major no-no!

MARY:   Oh, yes he did. Even asked when last time I had sex.  That’s when I said I thought he was getting too personal.  They’re all stupid.  Haha.  Well, no, I don’t really mean that.  But wow, most really have no clue.

CARRIE:  I would have hung up on him. How is that even relevant to a first conversation???????

MARY:  Technically, it was our 2nd talk, but first one was super short because he caught me working and I couldn’t talk long.  Anyhoo.

CARRIE:  It should never come up. Ewwww….girl, I wouldn’t accept another call from him. Like, ever.

MARY:  Dammit, he is so hot in his pictures…maybe I should just use him for sex…

CARRIE:  That wouldn’t be good, either.  Can you imagine him in bed?  He would still be asking questions:

Do you like this?

How am I doing?

How long does it take you to have an orgasm?

How long have we been doing it?

Am I doing something wrong?

Yuck!!!  I just had a horrible visual in my head…  He won’t even be worth it.  Girl, he was rude.  I have guys here who are interested in me and who would never even think about swearing around me.  You need to find a man who will honor you, not play 100 questions to see if you are good enough for him.   He’s got it all backwards.   HMPH!

MARY:  That’s sweet.

CARRIE:  It’s all about what you will tolerate and command.  First, second, or third conversation with someone you don’t even know, shouldn’t feel like a damn interview.  He should have been trying to get you to like him, not the other way around.  Welp…now you know why he is single.    Next!

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