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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


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