Love Letters: It’s 2017. Is It OK For A Woman To Ask A Man Out?

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Winter Cuffin’ Season is nearly in the rear view, which means spring fever will soon be upon us!

And when the pollen comes out, some of y’all lose your minds.

Before you get caught up, let your boy rein you back in.

Send your inquiries to, or find me on Twitter @etbowser. Just provide your initials, or a fun nickname. 

Here’s today’s question:

So I was approached by a young man I went to high school with. I made a remark on his Facebook post. His post asked who was off today and who wasn’t. I said I was off. He then inboxed me asking why I didn’t take him to breakfast because we were both off. I didn’t know if this was supposed to be a flirty thing or what. When I made a statement that he should be taking me out because he’s the man he in turn said it’s 2017, I can take HIM out. My question is: Should women take men out on dates since it’s 2017? Call me old fashioned but I don’t think women should be taking a man out unless they are booed up or married.


Shout out to our girl KJ who always comes through with the hard-hitting questions.

And shout out to her lame dudes, who always provide plenty of blog fodder. Y’all the real MVPs.

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Speaking of lames, let’s get to the brother in question. I wouldn’t burn too many brain cells analyzing his “guurl, when you taking ME out?” spiel. It was just an awkward attempt at breaking the ice and being funny.


But, as you mentioned, the convo did spark an interesting issue – is it OK for a woman to take a man out on dates?

Well, it’s 2017, why not?

I’ll spare you my usual analysis of our society’s gender roles, where household chores are typically determined by which sexual organs you have. I mean, whether you’re carrying the family jewels or possess a lady purse, the toilet needs to be scrubbed – who cares who is “supposed” to do it?


Now I know that’s easy for already-married man to say and is a much tougher sell for daters, especially when grandma n’ dem have beat into our brains that a good woman patiently waits by the door until that good man shows up on her porch with a bouquet of roses in one hand and the Holy Bible in the other.

Courtin’ is what they call it. And there’s nothing wrong with that.

But there’s nothing wrong with shaking up the system, either.

Now, I’m not saying you should Dinner ‘N A Movie the first brother who crosses your path in Target. Those gender roles are deeply embedded in our culture – going against that grain may turn off some folks initially. So while I’m certainly NOT against women asking guys out on dates in 2017 – and encourage any woman who wants to do so – it’s probably an easier sell to do so after a relationship has already been established. Once you and your boy are on friendly terms, there’s absolutely nothing wrong with asking the brother out and, yes, even picking up the tab.

And if he declines because HE’D rather handle the bill, that’s cool too.

Hold on to that dude, he’s a good one.

But the one key takeaway from KJ’s question is this – that dude who inboxed her is a cornball.

Y’all in the mood for one more question? Good:

I’ve been dating a young man for about two months. He was married for six years and recently got out of a relationship before me. He acts like he likes me but he’s always saying things like “I know a lot men like you. You have a lot of fans. I know a lot of men are after you in these streets.” He recently lost about 100 pounds. He seems very insecure. He says he just got out of a relationship. I don’t know if this insecurity act is genuine insecurity or if it’s a cop out to not wanting to be attached. Help!


Unlike KJ’s boy above, where that guy’s bluster was clearly part of his “game,” this situation is a little tricker. You can look at it three ways:

  • Homie is giving you a subtle compliment. Of course guys HAVE to be chasing after you, with you being so beautiful and whatnot.
  • He’s testing the waters. If you reply “well, yeah, I get a lot of attention from guys,” it shows that he has a lot of competition on his hands – and he might not be willing to fight off 100 other suitors. Plus, it’s a way to gauge your ego too. Conceit ain’t cute.
  • And yeah, not to get all Professor X with the psychoanalysis, but there likely are some insecurities going on here too. As much as women talk about how difficult it is to date, men often feel just as pressured – from their physiques to their finances. The struggle is real for errbody.

So, I don’t think his sheepish attitude is a cop-out. I mean, if he didn’t want to talk to you, he wouldn’t be talking to you, right? Instead, this is a weird mix of insecurity and weighing his chances of taking things to the next level.

So now lemme hit YOU with a question – do you want to reassure this guy and massage his ego, or will his insecurities cause you headaches later on? Ball’s in your court, playa.


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