EPIC Dating Failures! (Mothers, Catholics & Sisters, Oh My!)

Old, ornate, gothic-looking church

For the record, let me just say that I don’t give a flying fig about what two consenting adults do behind closed doors. Truly.

My Mom & Six Sisters Messed Me Up:

Quite a few months later, I was working in Colorado on a project, but was texting – on a dating site – with a man who lived about 100 miles from my house.

Welcome to Colorful Colorado

He seemed pleasant and interesting. 

He held a managerial position within the same industry, so we were able to incorporate a bit of light “shop talk” in our texts. 

Remember, people like to get their “crazy” out there right away.


They want to see if you’re cool with their particular brand of crazy, as soon as possible.

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His particular crazy was cross dressing, but he was testing the waters before he came right out and admitted it.

Male crossdresser with umbrella

Him:  “I was raised in a Catholic family by my mom with six sisters.  My dad died when I was 20.”

Me:  “Oh, I’m sorry to hear about your dad.  I can relate.  My mom died when I was a teenager.”

cemetery with headstones

Him:  Ignoring my response…Are you a girly-girl?  You know…do you like to wear lingerie and hosiery?”

opaque black panty hose

Me:  Understanding that there are a lot of less-than-feminine-looking women in our industry…”Sure.  I’m a girly-girl on my time off.  I like to look like a woman.”

Him:  “I love the feel of hosiery against my skin.  Don’t you?”

sheer hosiery

Me:  “I’m not comfortable talking to a complete stranger about sex or anything sexually explicit.  That’s not why I’m on this site.”

Him:  “Oh, I’m just asking because I really do love the feel of hosiery against my skin.”

pulling black sheer hosiery

Me:  “Yes, you mentioned that.”

Him:  I’m a regular man.  I think that lingerie is super sexy, too.”

black and peach lingerie bra

Me:  Becoming agitated for having to repeat myself… “Again, I’m not comfortable with this topic of conversation.  Have a good afternoon.”

Him:  “Wait.  I’m sorry.  I just thought I’d put it out there that I’m a normal guy.”

back of man head and shoulders

Me:  Wondering why he feels the need to restate that he’s “normal”…”What gives you the impression that I thought that you weren’t a normal guy?”

My mistake.  I should have just wished him well, and went on with my day, after blocking his profile on the site.

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Him:  Well, like I said, I was raised by my mother with my six sisters.  I was surrounded by women, and I love women.  I love everything about women.  I love the way they look…the way they move…the clothing they wear…everything.  But I was raised in a Catholic home, which is very restrictive, so I had to keep my thoughts and feelings to myself.”

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Me:  “I’m not sure what you’re referring to, and I’m certainly no expert on Catholicism, but I’m relatively confident that Catholic, heterosexual men are not frowned upon by the Church.”

Church steeple

Him:  “You’re not understanding what I’m trying to tell you.”

Me:  “Obviously not.”

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Him:  “I like the way hosiery feels against my skin when I’m wearing it.

Black stockings

Me:  “Okay…have a great day.  I’m done with this conversation.”

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Before I could block his profile and never hear from again, I received this message:

“I love to dress like a woman.  I wear lingerie to work sometimes, under my clothes.  I love to wear hosiery.  This is all my mom and sisters’ fault, because this kind of clothing was all around me, while I was growing up as a Catholic.”


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For the record, let me just say that I don’t give a flying fig about what two consenting adults do behind closed doors.  Truly.

Whatever puts a smile on your face is a good thing, in my book.

Happy Smiley Face GIF by Anne Horel

I suppose I’m old fashioned, because I believe in dating someone and taking some time in getting to know that person, before the inhibitions come out and the clothes come off.

couple embracing

To each, their own. 


At least give a girl the opportunity to get to know you, before you spring your three-alarm “freak” on her.

Freak GIF by memecandy

Let your girl decide for herself if she wants to get you in her closet and dress your ass up, all fancy — right down to your painted toes.

crossdressing tv land GIF by #Impastor

Dropping that news on an unsuspecting woman who has known you for all of five minutes will you get your thong-clad ass blocked, each and every time.

Guys, if a woman tells you that she wants to get married in the first five minutes, wouldn’t that scare the hell out of you?


Don’t give up.  Granted, there are tons of toads on the “dating scene.” 

toad in puddle

Don’t kiss them all.

You’ll get cold sores.

One thing I’ve learned through my online dating experiences is that there are tens of thousands of single people, in our age group, who are ready to meet someone.

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Of this, I am certain.

Sooner or later, I’m going to meet the man who wants to get to know my freaky side. Yep, I’ve got one, too.


freaky rob riggle GIF by Comedy Central

I know this to be true, as well:

First, you must establish trust.

Second, you must communicate openly and honestly.

Third, you must have a foundation, upon which to build.

I truly believe it’s that easy.

But what the heck do I know?

I’m still single, too.

Good luck!

(And don’t give up!)

More soon,


Restart. Refocus. Reinvent.

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