Skip to main content

Dear Troy - "How Deep is Too Deep on a First Date?"


Dear Troy,

I am officially back on the Dating Scene! But I really need to know... How much is too much to ask on the first date? Is income off limits ? Sexual history?


Dear Ms Neva 2 Much, NEVA 2 MUCH!! (sorry... had a "Lufa" Vandross moment lol)

Well first let me welcome you back to this crazy-ass-2020-newaged Dating Scene! Where anything is possible! Even dating robots...not that I have tried or anything, I'm just saying it's available...
But I'm thinking you're into humans, so here we go!

You are asking the right guy because I wrote the Book on Dating! "But, ...Naked Honest? Conversational Foreplay For Dating...Asking the Hard Questions Upfront" is literally the title!! So to answer your question, I don't think any question is TABOO on a first date. I mean honestly, what have you got to lose on a first date... but maybe a second date. My mentality is that you should ask and answer every question of significant importance on the first date. I am dead serious. Because then, you can make an honest decision if there should be a second date. And furthermore if this person even fits with what you want out of the possible relationship.

Now how you proceed with this is up to you. It's all up to you. Is this date just fun, dinner, and drinks? Very casual? If so, then you can keep it surface. If you already know you're not looking for anything serious then you can "Keep it lite" convo. There's no need to open up if you don't plan on being around. Dating can be just fun, no real pressure. And it's good to let the other person know upfront, usually during the phone call, text or video message that leads to the date. I told you, 2020 gives you 15 options on how to communicate with one person; ...yet communication is still hard?

Ask yourself, "What's my intent?"
Your intent should govern your questions. If you are dating to find Mr. Right - what is Mr Right to you? Does he have to have a certain income, car and home? Does he have children? Has he been married? Does it matter if he had numerous sexual partners prior to you? See once you ask yourself these questions, and answer yourself honestly, then you can decide if the guy fits what you want. I don't think there is anything wrong with wanting what you want. Especially if you are of a certain age (40+, 50+, 60+...) and know you want a serious relationship or marriage, time is of the essence and you've probably been through enough bullshit!

What I talk about and teach is HOW to ask questions without making it seem like a damn interrogation room. You're not a police officer or his drill Sergeant...unless you actually are one, then my apologies... and thank you for your servicešŸ˜€
Women are the most wanted creatures on the planet! Everybody wants one or wants to be like one lol. Just being womanly, in your own way, is attractive, inviting, and sexy. So unless this is a blind date, the guy is already attracted to you. And if you've had convo over the phone, he is obviously interested enough to want to engage further. Here are some ways to interject your questions in a fun conversational way:

  • Instead of HOW MUCH DO YOU MAKE - "What Kind of Work do you do?"This is really just a general conversation. We ask this to strangers in the grocery store who we end up talking to while waiting at the Deli counter. While he may not divulge how much he makes, if he can't tell you where he works or HOW he makes his money that's a red flag. And more than likely you'll tell him what you do too and the conversation goes on.
  • Instead of WHAT'S YOUR SEXUAL HISTORY - "You probably had all the women after you...didn't you?" Let me be clear, if y'all are flirting and the sexual chemistry is on 10, and you might even be sexting... there is nothing wrong with saying "Do you have and STD's or STI's I should know about?" - Because if he wants to have sex with you, you have every right to know! Shit nowadays you want to make sure he's Covid negative before you even meet. If there is chemistry and attraction there, it's easy to slip in little inquiries during the conversation.
All in all, I don't believe any question is off limits when dating. Be it the first date or 15th date, ask away! But if you really like him, put a little funny and a little honey on it. If you don't know, "HONEY" is that Sweet Femininity!

Until Next Time,

God Bless, One Love


Popular posts from this blog

It's Not Love, it's Love Adjacent

It’s my thought that the heart and the mind take turns in sharing authority in how we pattern our personal decisions. They cannot both be in control at the same time, and I believe that there’s a celestial straw pulling to determine which will rule within each given moment. The dangerous part about this is, sometimes when the heart wins, we forget to use our brain . When this happens, we start making decisions that are completely passion driven, hunger driven, and backed behind a receptor that shouldn’t receive as much showtime as it’s getting. Sometimes you fall in love with someone that is all wrong for you. They don’t feed you spiritually, they don’t feed you mentally, and maybe they don’t respect you. But they have ONE or two things on our list, so we keep them around. But by osmosis, all the signs that you saw in the beginning appear a bit less obvious, and now you THINK you love this person. Your heart is in control and your brain is taking a break, your brain has

Ladies, Make Him Act Right! (From a man's perspective)

So ladies, we have a tendency to get advice from women about MEN far more than we should. So I have a special treat today. We're going to get some advice on how to entice, encourage, and exalt a man from you guested it.. A MAN. I picked one, who speaks with the sole purpose to educate. So some of his language may be a bit harder than you're used to but.. you will not be disappointed. Capt SistaGurl Out!  Introducing Tikko Brohey  Ladies do you feel like “dudes ain’t shit” or “dudes don’t act right?” Have you ever thought about the things you do that contribute to that? The answer is probably not.  Now granted there are dudes out there who just ain’t shit, and that’s just what it is. Majority of men are good men. But his partner can often determine just how good he'll actually be. Every woman deserves to be treated like a queen, as every man deserves to be treated like a king. The disconnect comes from when there’s an argument all the King and Queen shit is out the

The Black Freak

Recently Nicki Minaj received a wax statue at Madame Toussads wax museum in Las Vegas. Although this is a huge honor, there have been recent reports stating that her statue requires extra security surrounding it. Spectators at the museum have been flashing photos of her likeness in very indecent poses.  Why? Well, because she's on all fours and half naked. Now, I've never been to this place but I went on the website, and viewed a few statues, the only other one half naked, but standing is..RIHANNA. Nicki Minaj in my opinion has willingly fashioned her persona into a modern day Sarah Bartmaan . For those of you unfamiliar, she is best known as the Venus Hottentot, and in life she was an African Woman turned Dutch, turned French tourist attraction, turned science experiment. This is real, look it up if you don’t believe me. Anyway, I say this about Onika because, like Sarah, when there was a rescue attempt to save her, she said (according to history),