Welcome to the taboo to Truth podcast, unapologetic conversations about sexuality in midlife.

I'm your hostess, Karen Bigman, certified life menopause coach, sex educator, and sexual explorer.

Whether it's a dwindling libido, dry vaginas, challenging erections, or the emotional ups and downs, we're here to talk about it all.

Ever thought it's just me?

Well, it's definitely not.

I'm here to bring the often quiet into the light to create a safe space where no question is too awkward or taboo.

Together, we are creating a community of support and education where you can learn, share, and laugh about the intricate beauty of sex and midlife.

We're about to embark on a journey of rediscovery brimming with grace, humor, and endless curiosity.

Let's tear down those barriers and celebrate the vibrant, evolving world of midlife sexuality together.

Because, yes, it's okay to talk about it, and yes, it's okay to ask.

So grab your favorite drink and put me on speaker.

It's time we broke the silence.

This episode is an interview with Alyssa Dineen, who is a dating coach, and it is an inspirational episode for all of us who are going back into the dating world.

It really resonated with the audience, with me, because she talks about the challenges of trying to figure it out and how she really wanted to just get right back out and start having sex, and the challenge that she faced trying to find a guy who wanted to actually have sex with her.

So this is a great, fun listen to.

I hope you'll enjoy it yet again.

In that I thought it was so.

Great, I wanted to replay it for you.

Welcome to the Taboo to Truth podcast, unapologetic conversations about sexuality in midlife.

I'm your hostess, Karen Bigman, certified life and menopause coach and sexual explorer, your trusted guide through the realms of dry vaginas, hot flashes, and the enigmatic orgasm journey.

I'm here to bring the often quiet into the light to create a safe space where no question is too awkward or taboo.

Whether you're experiencing changes in libido, concerned about navigating your menopausal life, or simply seeking to understand your body better.

Going to share this journey and it will be brave and open hearted.

And yes, it's okay to talk about it.

And yes, it's okay to ask.

So grab your favorite drink and put me on speaker.

It's time we broke the silence.

I have Alyssa Dineen here today.

She is a fashion editor, stylist, art director, and she got divorced at 41 began online dating, which started a really interesting journey of rediscovery.

And through this, she found that as a stylist, she was seeing a lot of pictures of people who don't look so great in their profiles.

And she was also seeing how challenging it could be to date in general and started a business around that called style my profile and is now helping online daters transform their destinies by taking charge of their profiles and their dating experience.

And I'll let her talk a little bit more about how she does that.

She is not only an acclaimed stylist and dating expert, but she's been featured in the New York Times, the Today Show, Goop, Oprah Dailey, and she recently launched a book called the Art of Online Dating, which we will put a link to in the show notes.

Welcome, Melissa.

Thank you.

Tell us a little bit about how you got here.

And I'm going to, you know me, I'm like, straight to the point.

Yeah, a little bit of the journey.

And then let's talk about the sex part.

You don't have to go into great detail how that informed how you approached dating.

I threw myself into online dating after, I think everybody says when they're getting divorced, I won't have to online date.

That's not me.

I won't need to do that.

But yeah, I did.

I threw myself in there.

Didn't really know what I was doing.

But obviously coming from a photography fashion background, I figured out the photos, navigating, messaging and getting on actual dates was, of course, a whole other can of worms and, but a lot of trial and error.

But I figured it out.

I went on nearly a hundred dates.

And after two and a half years, I met my partner.

Now we've been together almost seven years.

I met him online and when I met him, we both realized how challenging it is to online date when you've never done that before.

I think the younger generations are growing up with online dating or just social media and everything.

They're just used to all of that coming from long term marriages or relationships.

Neither of us knew what we were doing and we found each other.

And I realized there has to be so many more people like us out there that are challenged with online dating and just not knowing where to begin and how to navigate all of it.

So that's why I started style my profile.

All right, I'm going to back up for a minute.

100 dates.

Yes.

I've been doing this for a long time.

I don't think I hit 100.

Did any of those dates or this is, yeah.

That's including second and third dates.

Yeah, for sure.

A lot of first dates.

A lot of first dates, yeah.

I find that can be challenging just getting on the first date.

I have a friend who had an excel spreadsheet.

Good idea.

Really, it is.

I think the more you sample, the more you have a chance of finding the right one.

And I'm a huge proponent of online dating.

I am an online, I'm currently in the online dating world, and so I think it is the way to go.

And I'm very excited about what you do because one of the things that I see, I actually take screenshots of a lot of the profiles that make me laugh.

It's really unbelievable, actually, what some people put up there.

And you wonder, did you not?

I guess you didn't run that by anybody before you put that profile up.

There's definitely some doozies out there.

Talk to me, having been through this too.

How long were you married?

I was with my ex for about 18 years.

We were married for twelve, but yeah, we were together since.

Since right out of college.

Yeah.

Okay, so you meet a complete stranger that is theoretically vet someone vetted, and you go on a date and things start to heat up and you get interested.

How did that first sexual encounter, you don't have to give me, like I said, I don't even know, like, the details.

I was really unique, as far as anybody I know personally, in that I was really excited to have sex.

When I got out of my marriage.

We had a very, it was like a loveless marriage and it was pretty dull by the end of it there.

So I was really, I, the thought of having sex again with someone new was very, I was really into it.

I was very excited about that.

But it was really interesting.

And if you read my book, I talk all about this.

I couldn't get anybody to have sex with me.

No, there's a first.

Yeah, it was like, it was really funny.

It was, it became the running joke with my friends.

They were like, what is going on?

I'm like, I must be putting out a very desperate vibe or something because it was just one thing out.

Every person I tried to, wanted to bring home or go back, go back to their place with, it was like there was always something.

It was somebody had kids at home or they couldn't get it up, or it was any number of things.

Like, it was so many different things in a row that I was like, I am jinxed.

I'm never having sex ever, apparently.

So it was really funny.

It took me, like, five months of dating before I could find somebody to have sex with me.

It was actually.

It really was almost hilarious by the end of it.

It was like, are you kidding me?

How can you not find somebody in New York City as a female?

And so what were the reasons that they were.

Didn't want or they wanted to be in a relationship?

The first guy I dated, he was definitely not over his ex wife.

And every time we were alone, he came up with some reason why he had to leave.

He had sons that were in high school and college, I think.

So it wasn't like he had young kids at home or anything.

I had young kids, but.

So it was always some reason why he had to get home.

And that was like a month of that where I was like, I don't know what to say anymore.

I finally asked him and he was like, no, it's not that.

It's just I'm not ready to date.

And I was like, okay.

So that was that.

The next person, a friend of mine, set me up with him, and she said, I know you guys aren't going to be right for each other, so this is perfect.

Like, it was just going to be, like, just somebody to hang out with and have fun with.

And so he was the one who.

We went out on a date, he came back to my place, and then it was a flop.

Happens to the best of men.

I know, I know.

It was nothing.

It was nothing to do with either one of us.

It was fine.

But that was that.

And didn't see him again.

Not because I didn't want to.

I think he was embarrassed and whatever, but.

And then, yeah, and then it was like I would just go on a series of dates with people where it was just one thing or another that I just couldn't.

One person set me up with somebody else.

And, yeah, when he told me, he was like, I just think I want to be friends.

I.

This feels weird because we had friends in common.

Anyway, it was just all these kind of series of unfortunate events that led to me wondering what was wrong with me.

I really was.

I was like, I am definitely putting out some weird vibe of some kind.

Finally I met somebody and.

And he knew that I had this four or five months of trying to find somebody.

Yeah.

And we started calling it losing my second virginity.

So, yeah, then I finally found somebody, and then he actually blew me off after our first night together.

So that was not cool.

At least I ripped off the band, Aidan, and that was done.

I hope youre enjoying this episode.

Of taboo to truth.

Do you have any burning questions about sex in midlife menopause, dating after divorce, or exploring the spicier side of things like polyamory or kink?

I want to hear from you.

Head over to my website, taboototruth.com and fill out the form with your questions.

Ill answer them anonymously in upcoming episodes so you can get the scoop without revealing your identity.

It's like having a secret hotline to all your midlife sex questions.

Whatever it is, I am all ears.

So jump over to my website, tabutotruth.com, and let's keep the conversation going.

Now back to the show.

So how did you.

And this is one of the things that I am super nervous about.

How did you deal with STD's with when you had your first sexual encounters?

Did you ask?

I always use.

We always use protection.

And, you know, it's interesting because now that I'm coaching, I get asked that a lot.

Should I have the person get tested ahead of time?

Should I ask to see the test results?

And I guess that just wasn't really on my radar at the time, but in hindsight, I should have been doing that.

But yeah, I just use protection.

Yeah, it's interesting because you're not alone.

And I'm actually very surprised at how many people like, don't even think twice about it, including young people that I know that don't always think about it.

And I just met somebody new and I insisted on.

On the tests.

And he actually discovered, which is super interesting because this is something that, and this is not what this talk is about, but just on an aside, that he doesn't have herpes simplex two, which is the one that I am terrified of.

But he does have hs.

Hs one.

Hsv one, yeah.

Actually common in 70% of the population.

Of course he freaked out because he never knew and he never had a cold sore or anything like that.

Yeah, super important to be aware.

I always say it's not the condom is important, but you want to look and you want to look and you want to smell.

If those two things are good, then chances are the condom is adequate.

I just learned that recently that it's.

Yeah, like most adults, I think are.

Carriers or something and you can transmit it genitally.

I actually saw a profile, which kind of brings me to that, where the guy put on it.

I'm hsv two positive.

I have herpes.

And I thought I was very brave.

I would want to know if I was with a partner that had it.

I don't know whether I would actually get intimate with them.

That's really interesting that they put that on their profile, huh?

Because I know that gay men do tell each other when they're hiv positive.

Although today I think you just take a medicine.

Certainly back in my day, it was a potentially fatal disease, but still, they're very open about telling each other what they have or what they've been tested for or whatever, where it's just not a thing.

Talk about the idea of sex and midlife and what your perceptions were when you started the dating process.

I know you said you really wanted sex, but did you worry that your body had changed?

You were still younger than I was.

I was still pretty young.

But definitely being naked in front of a new person was terrifying at first, but I think that's just because I was with the same person for so long.

Not so much about my age or anything.

Most of my clients are there in.

In their fifties and sixties, and I would say a lot of women, I don't really hear it very often from men, but not because I don't think they feel that way.

I think they just don't talk about it.

But women feel they're nervous to do that for the first time.

Mostly because of the.

Not vanity, but that issue.

Not so much the sex part, but more just.

I can't believe that.

Seems really scary to be naked in front of somebody new.

So I talk to people about that a lot, and it is a hurdle.

But then once you.

I think once you do that the first time, it's okay.

I can totally.

I can handle this.

Yeah.

I find that the men were.

I know.

I have.

We all have our personal flaws that we're so conscious of.

I think they just, like, they just so much want to have sex.

They don't really.

I've gotten to that place.

I just.

Give me an opportunity.

I'm coming in.

You're not looking at your cellulite or your.

Your wrinkles or anything like that, that's for sure.

And certainly the maturer men, I don't date young men, but they also know you.

If you've had children, that they are probably parents themselves and they've seen their ex wives or ex partners.

Do you talk to your clients at all about the issues with menopause?

I've talked about taking a supplemental testosterone and using vibrators and things like that.

And it is always.

It's interesting.

This person I recently met, it's a very easy conversation, but most of the time.

So I just have something to tell you.

Before we get that kind of thing.

I know.

Do you coach your clients on how?

Yeah, I do.

Mostly I just encourage people to be as upfront as possible, and I think being honest about that and saying, this is my situation right now.

And again, most men in this age group are also have dealt with it or with their ex wife or whoever or other partners.

I think that it's not as.

As big of a conversation as we make it out to be in our heads, but I think it's just good to be upfront and honest and open about how you're feeling, really, with any sexual partner, about anything.

Not just about menopause, but really about anything.

And I know it's hard to do that at first, but I think that once you get used to doing that and having more conversations about it, it gets easier.

Is it okay to sleep with someone or to have sex however you define sex on the first date?

Absolutely.

I hate hearing how many people feel so questioning about whether they should have sex or wait for the third date or whatever.

I think it's.

And it does not matter.

I'm sorry.

If it's somebody that is, you're meant to be with and you guys are a good match, it doesn't matter if you have sex on the first date or the fifth date.

It's whatever is going to make you feel comfortable.

Of course, like, I think if you are into that, then yes, absolutely have sex on the first date.

When I think that whole thing where women are meant to led to believe that men don't respect you if you have sex right away, that I think, sure, that could happen.

But it's also if the person is meant to be, if the person is your person, they're not going to care whether you have sex on the first date or not.

So I definitely am a proponent.

I think you really need to know yourself.

I go back and forth.

I'm a very sexual person.

Obviously, you look at my line of work, but I also get very attached when I have sex.

As I start talking about this more and more, I've actually started to create a whole.

I don't know if it's a campaign or what I'm calling it exactly, but I'm doing talks on the definition of sex.

So I'm asking all my guests and starting to ask people, when you say having sex with the person on the first date, what does that really mean?

For me personally, I think that it means, like, getting very intimate, like your clothes off, oral sex, lots of body, everybody's exploring.

So whether or not you have actual intercourse.

I think maybe doesn't really matter in that situation.

I would say from that point, and then leading into intercourse would be.

All of that would mean sex to me.

I feel like if I have actual intercourse with somebody, it feels more like.

That feels more.

Okay, I know what you're saying.

That feels slightly more like maybe I'd be attached to the person in some way.

It's an individual thing, right.

It is.

Anything else you want to add about either what you do or, if not, how we all find you?

You can find me on my website, which is stylemyprofilenyc.com, or on my instagram, which is Alyssa Dineen.

And then there's another account called style, my profilenyc.

All right, well, thank you.

This was great.

A lot of good information.

I'm sure that I'm gonna get lots of questions after this one.

It was great to see you.

Thank you.

Thank you.

Thanks.

Thanks for joining me on the taboo to Truth podcast, where I'm spicing up midlife one episode at a time.

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It's time we broke the silence.