The Naked Advice

Model & Writer Liz LaPoint answers your questions about dating, sex, and relationships

Liz: “I’m happy we connected over Twitter a couple of years ago! I enjoy reading your balanced, reasonable, experienced answers to the letters you receive on your website

Demetrius: “Thanks Liz! I’m glad we connected on Twitter all those years back as well. I think you take a very balanced and reasonable approach to answering questions as well!”

Liz: “You live in Brooklyn, NY now. What’s the dating scene like there? Have you ever lived somewhere else, and was dating different there?”

D: “Well I think I’m at a bit of a disadvantage, or maybe it’s an advantage, when it comes to talking about dating scenes because I’m a lifelong New Yorker. I’ve lived here my whole life, and while I love to travel, I can’t picture living, or dating, anywhere else. When I say the Brooklyn dating scene is good, I can really only compare it to what I hear from other people and their experiences dating in other cities. I think Brooklyn, and New York City as a whole are great dating scenes primarily because they attract so many people that your dating pool will never get stagnant. I’ve met so many incredibly women from so many different walks of life, religions, ethnic groups, etc. that I honestly think I’m a little spoiled.”

Liz: “What is the ‘Tao of Indifference’?”

D: “So here’s a confession, the name of the blog originally comes from an inside joke amongst my friends. For years, way before I had an inkling of writing about dating and relationships, I developed a reputation amongst my friends of being pretty indifferent when it came to dating. Got rejected, no big deal. Girl broke up with me today, meet someone new later tonight. So when I decided to start the blog, I was brainstorming blog name ideas with a buddy of mine whose a marketing whiz. He came up with the name and the name stuck. To me, it’s all about having a little detachment from the things that are out of your control in dating and relationships, so that you can focus on the things you can affect. I think that’s what makes me successful in dating, and that’s what I want my readers and listeners to learn from me. Basically, “don’t sweat the small stuff”. You’re going to get rejected when you date, don’t focus on that, focus on finding someone who is a better fit for you.”

L: “You interviewed me last year on your podcast which was fun! Did you start the blog or the podcast first?”

D:It was fun, I thought you were a great guest and maybe the only one who I’ve spoken with at length about fetishes. I started the blog first, in January of 2013. Then the podcast in January of 2014. I would say that things really started picking up in 2015, because when I started I was just sort of winging it and learning as I went.”

L: “What’s the craziest date you went on?”

D: “Let’s go crazy good, and crazy bad, because I’ve been on a lot of different dates that turned out crazy in a lot of different ways. One of my craziest first dates, in a good way, was a date that lasted almost 12 hours. We met for drinks at around 7pm, started making out at that bar, then went to a wine bar after the first bar got crowded, started making out at that bar, then we went and got food at about 1am, THEN we took our food and did karaoke in a private room until 5am.

The absolute craziest bad date I went on, was a date where my date and I were mugged. It was a first date and we decided to hang out in a park to people watch and talk. By the time the sun had set, we were making out on a bench when someone approached us, got our attention, then said that he had a gun. We handed over what we had, left the park, went to her place and called the cops. It was more surreal than anything else.

Most of my dating life is way more mundane than these two dates, I promise.”

L: “What’s the weirdest or most interesting letter you received?”

D: “Honestly, most of the questions I get are fairly simple, and even the most interesting ones are really, at their core, fairly mundane. How soon is too soon to do something? Did I do something wrong? When should a certain dating or relationship milestone happen? Things like that.

The most interesting thing I’ve ever received on the blog, however, is a comment someone made on a post. I wrote about preferences in dating, around height, body type, race, religion, etc., and for context, the piece is about 1100 words. The person who commented left a 750 word comment on the piece where he said that the article was long-winded, and went on to essentially write fan-fiction about himself and how confident he was. At one point he used the the terms “naughty double advantage” and “naughty loophole”. It is truly bizarre and while I’ll never approve the comment, I can’t help but read it from time to time.”

L: “If you could go back to your teens knowing then what you know now, what would you do differently?”

D: Stop being so focused on having sex. I think that, like a lot of teenage boys, there was this vague societal pressure to have sex. I tried so hard to have sex early on, and tried to have as much sex as possible. I’d have been much better served if I had spent my teenage years trying to connect with women, rather than just trying to get in their pants.”

L: “What would you say is the biggest dating mistake men make and women make?”

D: “First, coming on way too strong too early on. Second, trying so hard to please people you don’t showcase your personality. Third, always looking for a better option. I think that will only become more and more true with the way people date online. I think that for the most part, these things are common between men and women.

My advice is this: if you feel like you come on too strong too soon, set boundaries for yourself that you stick to. That could be as simple as “I won’t text the next person I date 5 times a day if I have nothing to say”. If you’re trying too hard, it’s probably because you’re afraid of getting rejected, which is a bad idea. It’s always better to get rejected so you can find someone who likes the real you, rather than sticking around to be with someone who likes fake-you. Finally, if you’re going to date online, figure out the things you want and need in a relationship, what your dealbreakers are, and if you find someone who sounds like the person you described, take a leap of faith and give them an honest try.”

L: “Would you say it’s a good or bad idea to join dating websites that cater to something very specific, like religious affiliation or race?”

D: “I think that in some cases, it’s a bad idea to join niche dating sites, but in a lot of cases it’s not. It really all depends on how important your niche is to you. I love comic books, but I would never join a niche dating site that only caters to comic book fans. That said, if marrying someone who shares your faith is extremely important to you, it would make sense to sign up for a site or app that caters to your faith. The one thing to keep in mind is that most niche dating apps have very small user bases, so it might still be easier to find someone on larger dating sites.”

L: “Did you get any dating and relationship advice from your parents when you were younger?”

D: “My mother gave me a really good piece of dating advice when I was 9 years old. I had a crush on a girl in my class and I asked my mother what I should do. She told me to ask her out, to be myself, and if I get rejected remember that it’s not a big deal. It’s advice I give on a pretty regular basis.”

L: “Personally, what’s your biggest turn-off when you first date a woman?”

D: “Lack of confidence for sure. I don’t need a partner who is overly confident, I don’t need someone who is just irrationally confident at all times, but if a woman has no confidence in herself, it’s a big turn-off.”

L: “What would you love to see change in our culture regarding sexuality and relationships?”

D: “I would love to see more open, honest, and frank discussion about sexuality and relationships, from all walks of life. Just think of how infrequently you’ve heard about what sex is like after middle-age, compared to how much money is spent advertising erectile dysfunction medication to middle aged men. There are conversations around sex and relationships that are happening all the time, but I’d love to hear more diverse conversations.”

L: “We have a lot in common! Not only are we both in the business of relationship advice, but we are both of mixed race. Do you find being mixed presents its own challenges in relationships?”

D: “Haha yes! We’re two peas in a pod! I definitely think that being mixed, dating interracially, or just interculturally, presents it’s own challenges. Even in a best case scenario where you meet someone who doesn’t share your background, but is open to learning about you in an earnest way, there is still a certain amount of challenge there because you don’t share the same cultural shorthand, for lack of a better term. Sometimes it’s bigger stuff, and sometimes it’s as small as explaining to someone that I grew up singing Stevie Wonder’s Happy Birthday song on birthdays.

In my experience, if you’re dating someone who is open-minded, the challenges can be overcome. I’ve dated people from all races and ethnic groups, from all sorts of backgrounds, and each one comes with it’s own challenges but, and this might sound cheesy, but love conquers all.”

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3 thoughts on “NYC Dating, Getting Mugged, & More With Dating Expert Demetrius Figueroa

  1. RedSportsCar says:

    Great interview, really enjoyed it! Living in a smaller town outside of a semi-major metro, it’s great to get this sort of perspective.

    Liked by 1 person

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