Interview with Back in Stilettos Again

Welcome to the third in my series of interviews with interesting people navigating the strange and unpredictable world of online dating, aka modern dating.

Lauren, firstly I’d love to hear in your own words why you started Back in Stilettos Again and how you describe it?

Thank you, Eve! I started my blog because I was new to dating after my 16-year relationship/marriage ended. Online dating had changed A LOT since I’d done it back in the late 1990s! It was extremely entertaining and I remember telling some friends, “After two weeks online dating, I have enough material to write a book!”

The propositions were outrageous and it really opened my eyes to the dating underworld I wasn’t previously aware of… such as kinks, fetishes, and outright foolish behavior. Lots of guys would simply contact me on OkCupid to play games… and at first I was naive. It blew my mind that some people had that much time on their hands. I was also overly eager because I was touch-deprived after getting out of a sexless marriage.

I started my blog as a diary of my dating adventures. My slogan was Diary of a San Francisco Serial Dater, because I was on a focused mission of finding someone who knocked my socks off. Within two months of starting the blog, I unexpectedly found myself in a relationship with one of the first guys I met online after splitting from my ex-husband.

Unfortunately, I didn’t start the blog until six months after I had started serial dating and, as a result, lost out on documenting a lot of fabulous dating stories.

I recently changed my blog’s slogan because I’m no longer ‘serial dating’. I’m now taking a more deliberate, careful approach to dating. After 3+ years of awesome sex, I’m no longer constantly touch-deprived. Of course, I still have a very high libido… but I’m no longer trying to make up for lost time when it comes to touch…and that fortunately takes a lot of pressure off the dating process.

So, to make a short story long, my blog is a diary about my dating adventures. I write about dating, sex, love, relationships, and self-discovery. The simple act of writing helps me discover a lot about myself!

You’ve been dating again after marriage and kids for three years now, what have you learned as a standout lesson, and what are some of the smaller ones?

I have dated A LOT of guys in the past 3+ years. In the first six months of post-marriage dating, I met 55 new guys. Now I’m guessing the number is around 80 (I was off the market for several months while in two long-term relationships). And this isn’t even counting the 100 or so guys I dated through my late teens and 20s. I’m experienced! I’ve always loved dating – It’s fun, it refines your social skills, and it teaches you what you do and don’t like.

Lesson #1: The perfect match doesn’t exist. There is no such thing as a ‘soul mate’. I’m sorry to disappoint the teens and 20-somethings who are reading this!

The biggest lesson is that the perfect guy… and even the perfect guy for me… doesn’t exist. Some guys will obviously be better suited than others but it’s all a sliding scale. Figuring out what I will and won’t accept is tricky because I have to take some bad qualities with the good. Always. So the battle becomes: “Can I tolerate the thing(s) I don’t like?” And then there’s the whole phenomenon of change. People change. I made a good choice marrying Mars and don’t regret it one bit… but we both changed and ultimately became incompatible.

I highly recommend that every single person looking for a long-term relationship date a lot of people! It’s a great way to learn about yourself.

Actually finding a relationship, on the other hand, is like magic: The right place, the right time, the right physical attraction and chemistry, the right values/morals/goals, and the right compatibility. It seems damn near impossible. No wonder it always seems so unbelievable when it actually happens!

Lesson #2: I don’t think I believe in marriage. I believe in healthy committed monogamous relationships, but I believe they have a shelf life and aren’t necessarily meant to last forever.

Lesson #3: Finding someone I like who is compatible and who doesn’t annoy me is pretty damn difficult. I’m an easy-going, naturally curious person so this was surprising. People are quirky! Interpersonal relationships are complex!

There are probably a lot more lessons but this is all I have right now. Haha.

With your expertise are there types to watch out for or avoid? And for what reasons?

Nah. It’s all a matter of personal taste. I have my own preferences and my own type… and “what I’m looking” for has changed over time, too.

That said, there is one tip I’ll share here on how to spot a catfisher. I was catfished once back in December 2014, and there was one major red flag in his profile that I should have been suspicious about: All seven of his profile photos seemed professional (great lighting, great angles, etc). They were also only of him solo – none of the photos included family or friends. Well, after he stood me up I did a reverse Google image search on one of the photos and learned that the photos were of a famous Indian actor.

What are the issues as you see them for women in their 40s or older dating again after long-term relationships and perhaps children?

I honestly don’t see any issues with women dating in their 40s UNLESS the woman has kids. With kids and full or partial custody, scheduling dates can be problematic. Otherwise, dating as a woman in your 40s is better than ever. You don’t have the pressure of wanting to choose a life partner and start a family. In other words, you no longer have the biological clock pressure so dating becomes a lot more fun and carefree. Freedom!

I love the way you detail some lifestyle touches in your blog, I feel as if I learn a little about the San Francisco area a little more each time I read it. The pieces have a diary feel to them – is this intentional? How have your blog posts changed as you’ve grown more of a following?

Yes, I definitely started the blog as a diary concept and I’ve maintained that over time. I occasionally throw in more ‘article’ type posts if I think it might be helpful for readers looking specifically for dating advice or if I think I may have something helpful to share.
The content of the posts hasn’t changed much, if at all, over time as the blog has grown and I have more readers. I write for myself, using it as a tool to document my memories… but I love that there are other people rooting me on, offering great advice, and keeping me accountable. I’ve been both admonished for acting like a jerk and comforted when going through heartbreak. I let it all hang out – It’s my real life. I’ve developed some fabulous friendships here and I’m so thankful for the WordPress community.

You mention aggressive serial dating as your sometime approach – what do you mean by that, and what is your preferred modus operandi? I guess what I am saying too, is what is your ultimate goal?

When I’m single, I tend to take an aggressive serial-dating approach. It’s hard for me to do something halfway. When I want a boyfriend, I want a boyfriend now and I’ll get somewhat obsessive about it until I either find my flame or get burnt out and take a break. Ideally, I would take a more relaxed, leisurely approach but my personality doesn’t lend itself well to that. I’m pretty Type A.

I’m a hopeless romantic and tend to think my next heart-throb is right around the corner. I love love, and I love being in love. It’s a natural high! Love is the drug.

My goal is to find romance and passion with someone who rocks my world.

What are the apps you recommend and those you avoid? Have you found a different type of clientele on each app? I know from reading your posts that you’ve had the most success with Tinder? Any thoughts on why that is?

I’ve actually had the most success with Ok Cupid. It’s where I met my post-marriage boyfriends Tex and Hayden and where I also met Joaquin (an ‘almost-boyfriend’). I haven’t met any boyfriends on Tinder… yet! I prefer the Tinder interface over the Ok Cupid interface, though. I love its simplicity.

I haven’t found a different clientele on any of the apps and actually find many of the same guys on several of them. I think they like to keep all their options open, as I do.
That said, there are several dating apps I have tried and didn’t like at all: Zoosk, Coffee Meets Bagel, Happn, and Once. I know Bumble is a popular dating app but I personally don’t care for it. Every dating site and/or app I’ve tried are all mentioned on my blog.

You write about your sex drive dramatically increasing at age 38 (when you were unhappily married). I’ve encountered the same and read about the huge increase in sex drive in premenopausal women (which can be any time after about that age until mid-50s). How has this affected your approach to dating and what you’re looking for?

Oh boy. Hahaha. My massive libido made a big impact on how I dated immediately after splitting from my ex-husband! I almost found it to be a disability. I was inexperienced in the current dating world and was also a bit desperate to feel adult human touch…. which made me a lot more tolerant than I would have been otherwise. Granted, I didn’t want a relationship with anyone at the time so anything went. I simply wanted to make out, grope, and/or have sex with a relatively nice, normal, fun male human.

It took me a while to figure out what I would and would not tolerate, and what I really wanted. I was occasionally chatting with a guy who had a fetish for impregnating women. I regularly chatted with a bisexual guy who wanted to have a BDSM threesome with me and another guy. And there were a couple of guys I briefly dated who were polyamorous and in open relationships.

This was all completely new to me and nothing like I had experienced when I was in single and dating in my 20s.

I was fascinated by it all at first. Over time, though, I realized what I really wanted: An emotionally intimate monogamous relationship with one special guy. And I ultimately realized that I’m pretty vanilla. Sex is awesome on its own; I don’t need props, fantasies, or elaborate scenarios (although I do acknowledge that I might re-visit that if/when I’m with the same guy for several years and want to shake things up).

You say that before your marriage ended, you felt lonely, ignored and invisible. I know for sure that A LOT of women in long-term relationships feel the same way, whether or not their relationships end. What are the challenges of starting again after this phase, and how do you reconcile your needs with all the other factors at play – kids, ex, time alone, hormones/sex drive and meeting new people who aren’t necessarily on the same page or sexual groove?

I feel like I lead a double-life. I’m a single, carefree woman with a very busy social life half the time and am a responsible mom the other half. My child-free time is spent staying out late, flirting, meeting lots of new people, and having sex (hopefully lots of it!) while the time with my kids is spent staying in at night, cooking meals, overseeing teeth brushing and bedtimes, and often going to bed early myself.

The split lives are such a dichotomy. I think part of the reason I love relationships so much is that I can merge these two different lives. I feel my time spent in relationships is much more balanced.

If a guy I’m seeing isn’t on the same sexual page as me, well it’s simply not going to work out. Sex and intimacy are extremely important to me. Sex is a fabulous stress-reliever, too. It would downright suck to have a boyfriend who couldn’t keep up with me sexually. I just can’t see it working. It’s important for me to be with someone who places just as much value in it as I do.

You say that writing our your thoughts and feelings is way to understand yourself and process events in your life. I think we can all relate to that. I like the ways you credit your readers, too, for helping you see something differently. I feel the same way, even after only a month or so of running this blog. Can you share an example of how a reader’s perspective changed your view or helped you see a situation differently?

Readers’ own personal experiences with alcoholism really helped me navigate how to proceed with Hayden after he admitted to being dependent on alcohol. It was really eye-opening. Just hearing everyone’s perspectives really helped me be more supportive of Hayden and more aware of the illness’s limitations.

What are your thoughts on marriage and monogamy after being married and then almost being married? Do they go hand in hand? What do you strongly believe in about your future needs and wants in relationships and what do you think is problematic?

I am a huge fan of monogamy. Huge! A big stressor for me when casually dating is the risk of sexually transmitted infections. They can happen even if you use condoms! Condoms aren’t foolproof. And let’s face it: condoms suck. Nothing beats skin-on-skin. Condoms are a necessary evil until I’m in a monogamous relationship, though.

I was always faithful in my marriage despite being sexually unfulfilled. I never considered having an affair. I did, however, tell my ex-husband that I was considering looking outside the marriage if he couldn’t at least try. And so he tried… but it was a half-try and only done out of fear of losing me rather than truly wanting intimacy. It felt forced and emotionally vacant. It screwed with my self-esteem and ultimately wasn’t enough anyway. I wanted more. I wanted passion, romance, fun, and most importantly connection. Life is too short!(Just to clarify, the lack of sex and intimacy were symptoms of bigger problems in our marriage.)

I want a monogamous, emotionally intimate relationship with plenty of hot passionate sex.

The problem I foresee with a future relationship is that I tend to become anxious in relationships… and it always revolves around texting communications. It happened in my relationships with Tex and with Hayden. I’m trying to figure out why it happens and how to prevent it from happening again.

You say that perhaps you have never had a relationship that wasn’t dysfunctional – don’t you think that applies to most of us? You’re also pretty hard on yourself (quote: I freak out, over-react, and get spooked easily. I overthink. I need to calm the fuck down and relax.) OK here’s the hard bit – what are your BEST features and what would make you an AWESOME catch for some lucky dude?

If you really think about it, yes, almost any relationship is dysfunctional… just like almost every family is dysfunctional. We’re all imperfect with our own quirks. Just because a relationship is dysfunctional doesn’t mean it won’t work, though! It might work very well for the couple in it.

As for me, I’m an incredible catch! I am a friendly, genuine, approachable, happy, stable person. I have a fabulous ‘cool’ job in an architecture and engineering niche that constantly challenges me. I like going to work every day. I am great at managing my money, am financially savvy, and live within my means. Health and fitness is really important to me; I don’t take it for granted and constantly push myself to become better without being obsessive about it. I am attractive thanks to good genes and taking good care of myself my entire adult life.

I’m intelligent, educated, and a reasonable person with sound logic. I have a wide range of interests and know a little about most topics even if they’re obscure – I’ve dazzled past dates and boyfriends with my knowledge of what vector causes Lyme disease, knowing what ‘alba’ means in Latin, and how to ask for water in Mandarin. Haha. Most importantly, I am very devoted and loyal when I’m in a relationship. I’m like a dog!

What’s not to love?! Haha. I’m currently accepting applications for my next boyfriend.

How do you navigate the timing to get off the dating apps after you meet someone you think has serious potential? Do you discuss exclusivity first? Do you quit the apps and wing it? And how do you know if he’s not secretly back on the apps, or never quit? The dating world got a whole lot more complicated post the internet!

I close down dating apps only after falling in love whether we’ve had the exclusivity talk or not. I just don’t feel comfortable chatting with or dating potentials when I’ve told another guy I love him. It’s not fair to anyone. The exception to this was Tex… and I didn’t discontinue the dating apps because he was pro-polyamory and I knew I ultimately didn’t want a polyamorous relationship. So I told him, “I’m looking for something monogamous but I’ll continue dating you in the meantime.” I loved him but he couldn’t provide what I wanted or needed. (He eventually changed his mind and wanted monogamy… at which point we both closed down the dating apps.)

Otherwise, I use my intuition. If the guy seems completely devoted to me (ie Hayden) and is so busy seeing me that he wouldn’t have time to see anyone else, I don’t worry about it. Hayden and I never had the dating app talk because he admitted he wasn’t dating anyone else.

I was interested to read about what you describe as your low level anxiety. I suspect we’d get along just fine! And also that we’re both introverts? I’m immediately curious about how this anxiety pans out before dates, and before sex dates in particular. I have noticed an unhealthy pattern myself and I’m trying to deal with it.

I don’t have any anxiety when it comes to dates or sex. Dating and sex are the fun, easy parts! The worst part about dating for me is when I’m simply tired or suspect the date might be a dud and then I have to psyche myself into going. Relationships, on the other hand, tend to bring out my anxiety. It sometimes makes me wonder why I even want to bother! Interpersonal dynamics are so complicated.

On a personal note I’m also interested in how you negotiate sex and whether or not it will happen.

The only times sex is ‘off the agenda’ on a date is when I have an active yeast infection or a bacterial vaginosis infection. Otherwise, it’s always a possibility! If we’re both feeling it, it’ll [hopefully] happen. And if I’m not feeling it, then it typically doesn’t happen. I say ‘typically’ because there was one time I felt bullied into having sex and then I gave in only because I wanted to get it over with and leave without him harassing me further. It was icky.

How do you manage what to tell friends and family about your new post-marriage life? I enjoyed reading about some of the challenges and judgements in the past. Do you keep your dating life to yourself, let it all out or somewhere in between?

I have mostly kept my dating life completely to myself. My family knows nothing but that’s only because they don’t care to know. My friends know a little. Mars knows a little. One friend – actually my ex-boss – knows about my blog but she doesn’t read it. Several online friends know about the blog and are regular readers. My ex-boyfriend Tex accidentally found out about this blog right after we became exclusive. Needless to say, shit hit the fan hard. It was emotionally devastating and nearly broke us up. In hindsight, we should have ended the relationship then because I don’t think the relationship ever recovered.

Mine is a secret blog and I intend to keep it that way. I would be mortified if anyone I knew found out about it.

Finally, we’d better touch on cougars! What do you think of the whole cougar mythology? Do you ever use that terminology yourself? I know from experience that you like younger men – can you tell me why, and your thoughts on younger vs older and the issues with both?

I don’t like the term ‘cougar’ and definitely don’t use it myself. I like all men! But I’m kind of like Baby Bear in that they need to be ‘just right’… not too old and not too young. I seem to have the best luck with early 30-somethings. They’re not bogged down with life, they don’t have big responsibilities like mortgages, child support/spousal support payments, and child custody schedules. They are still enthusiastic and passionate. And they tend to be responsive text communicators.

I look younger than my age and I think my energy level simply better matches with men in their early 30s.

Older men tend to be lazy with dating and look much older than their age unless they’ve taken immaculate care of themselves (and most men just haven’t). They are also more set in their ways, tend to be harder to get along, and are pretty judgmental.
I recently wrote a long post about my theories involving the pros and cons of younger vs older.

Thank you so much for interviewing me, Eve. This was fun!

Thanks to Lauren for sharing her views and feelings on so many intimate topics. If you haven’t seen her blog before, head on over to Back in Stilettos Again.


36 thoughts on “Interview with Back in Stilettos Again

  1. What a GREAT interview! Wonderful questions, & fascinating answers 😃. You two were fab- you should do a podcast together or something- ‘dating around the world for the over 40s’. I really really enjoyed that, congrats to you both 👍🏼❤ G

    Liked by 3 people

      1. Nina told me about one that I actually listened to…. but it was a short 6 episode podcast so it was more do-able. Still, not easy for me to do. I’m more of a reader than a listener. LOL


  2. This was great fun to read! I loved the comment for the young people who think there is a soul mate.
    Not there, people! The silver chalice or golden ring does not exist. If two people (or more) can communicate and live happily and successfully, your goal is reached!

    Liked by 2 people

      1. I know some folks who are still married to the one they dated first in HS. But, they are few and far between!!!!!!
        Soul Mate is a click bait phrase and annoys me!


  3. Yes, exactly! Success should be measured by finding someone who doesn’t drive you bat-shit-crazy! At least that’s my goal. 😉 And I’m a fairly easy-going person so that’s saying something.

    And I think Eve is right: Many older people think this way, too, if they don’t have a lot of relationship experience.

    Liked by 1 person

      1. Really me? I’m so boring at this point. Nothing like your last person! There’s no story here for me, yet. But…when I do have one, I’d love to participate! In the meantime, it’s the doldrums here, yawn central, but hopefully life will become more interesting in 2018!!


  4. You’re so interesting! I do not think I’ve truly read through something like that before. So great to discover another person with a few unique thoughts on this topic. Really.. many thanks for starting this up. This web site is something that is needed on the internet, someone with a bit of originality!

    Liked by 1 person

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