Project 50 First Dates—When to Send The Dick Pic

Gentlemen, is There Ever Really a Good Time When to Send The Dick Pic? (You Might Be Surprised!)

Dating Site: none; met in the “real world”
Stats: early 40s, divorced, two kids
Profession: sales

My sixth first date and I go for a late breakfast at a big-ass breakfast greasy spoon café in Gastown. Like.

I originally met this fella back in December through a girl friend when I was helping her with a “career function” and some light, mutual text flirtation ensued between him and I … until I discovered that he didn’t meet my Top 5, at which point, the fun fizzled.

By the way, if you missed my live interview with Roundhouse Radio on how to figure out your deal breakers / deal makers and discover your Top 5, please click here for the instant replay!

If you like it and want Roundhouse to ask me back for more radio shenANNAgins, please share and tag RH and Wingmam. #shamelessplug

Anyway, back to Big Dick … and he wasn’t a dick, actually.

We had an easy-going, fun conversation a few days ago that had me wondering if I might alter my Top 5—danger! danger!—but I was saved because…

…after the “not really a date,” our text flirting escalated, and I wound up with a (somewhat artistic) photo of his penis.

To be fair, there could’ve been—obviously, there was—some misconstrued misinterpretation of whether or not to send the image of “his toes.”

What I thought of as side-smirk-innuendo-wink, he took to mean, “Yes, please, send me an image of your erection, STAT.” Which he did.

Rule #1 (and only) re: When to send the dick pic …

Send a photo of your penis only when she explicitly requests it.


Her: Please send me a photo of your [penis] 😉
You: Really??
Her: Yes! Totally serious.
You: Okay … he it comes 😉

Hint: Wait a few moments. Why?

  • In case she changes her mind (women do that)
  • To arouse anticipation
  • To have time to “fluff it up” (no one wants a limp dick pic)

If you send a dick pic too soon and without her request to a quality woman that you want to bed for the long term, she will think:

  • You’re immature.
  • You only want sex.
  • You’re an idiot—delete, do not pass go, do not come (over.)

In my case, I hadn’t seen a real live dick pic in so long that it caught me off guard, and I promptly saved the photo, but deleted the boy-man.

Let’s remember, I’m a quality woman looking to bed a man for the long term. (I’ll explain in another post why casual sex interferes with this goal for many women.)

I asked him some point blank questions, via text, that would see if he would meet my Top 5.

His reply: “This will cost you breakfast.” Followed by more flirting and averting.

Note: Had he the balls to answer my questions honestly and even had those answers been “wrong,” I might’ve considered a fling or a friends-with-benefits situation (read this article I wrote about flings vs. FWB)—even though it goes against my ultimate relationship plan (dual meaning)—because I haven’t seen a real live dick in a while, people!


  1. A gentleman looking for the long term saves sending the dick pic for after she’s already seen the real live thing in the flesh.
  2. A gentleman slowly escalates sexting based on the lead of the quality woman he wants a long-term relationship with.
  3. And a gentleman (now) knows that I only sell “long-term happy couple coupling frequently” ideas, and if you want to know how to wet-‘em-and-bed-‘em, this is not the site for you.

Finally, if Big Dick is reading this, please learn something and don’t be angry: I just told the world you have a nice penis.

xo AJ

p.s. Remember, it’s not the size of the member that counts. See Does penis size matter? video and subscribe to WingmamTV to receive new fun-ucational dating, love and relationship videos weekly. (Do it for your country?)

Here are some more ways I provide dating advice for shy guys & introverted men to get a girlfriend.  Wait, not just a girlfriend, but your dream girl. 

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Your Creator is your biggest fan and didn’t put you here to be shy, single and suffering. But, as My Little Mom (RIP) used to say, “God helps those who help themselves.”

Dude, you really do deserve to be loved.

To the very core of me I KNOW this to be true. It is the reason I do what I do.

And, guess what else? You don’t have to believe in God for my dating advice to work for you.

Follow my dating advice for shy guys & introverted men and before you know it you’ll get a girlfriend and be cuddled up on the couch chillin’ ‘n Netflix’in with your soulmate — no more Hands Solo!

Thanks so much for being here in the world with me! For reals.

xo Anna

Founder of Wingmam, Lover of Love, Your 2nd Biggest Fan!

You got this.

Um, yeah, here’s the fine print:

DISCLAIMER: Anna is not a psychiatrist—no way—or medical advisor—nope—you are responsible for your actions and the results thereof. Such is life.

About the Author Anna Jorgensen

Vancouver dating coach for men who love women! ❤️ (Not PC and not a feminist.)

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Dating 101: Top Dating Tips For Men Over 40 says January 5, 2017

[…] selfies of you in your tighty-whiteys in the bathroom mirror and def definitely don’t send dick pics! I don’t care if you own Park Place, that’s […]

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