Dating Advice: Unsolicited Dick Pics?

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Craig Asks: Hey UGS, how do I seamlessly weave this unsolicited dick pic into polite conversation?

Great question, Craig.

Look, we’ve all been there. You’re talking, she’s laughing, things are going great; then suddenly it hits you – Whoa. This woman has no idea what my penis looks like. Frankly, it’s embarrassing. Sure she’s acting like everything is cool and normal, but you know she’s dying to see a totally random and unprompted picture of those sweet, sweet genitals. Well, don’t make her have to ask for it idiot, send away! But first, some tips:

Tip 1: Remember – Angles, Lighting and Situational Awareness:

Do. Not. Matter. Send the dick pic already. She’s wondering if you really do have a dick at this point, and I don’t blame her.  Man up and send that picture of your kind of hard penis sticking out the top of your gym shorts with a toilet seat in the background you’ve been saving for a special occasion like this one. She’s fiending for it. She wants to see that D. Quit depriving her of it.

Tip 2: Catch Her Off Guard:

The less sexually suggestive the conversation, the better. What’s taking so long anyway? Maybe you should send her a vagina pic instead since you’re such a pussy. Click. Send. And. Ask. Her. What. She. Thinks. About. It. That’s right. Doesn’t that feel better? Now clear some space on your phone for the flood of nudes you’re about to get for reading her mind. You did the right thing, Craig. Breathe easy. We need you on your A game for when she starts sending those sexts.

Tip 3: Why Hasn’t She Responded Yet?

[Expletive]. [Expletiiiiiive]. She definitely read the message. Maybe she didn’t like it? No, no way. It’s your penis for crying out loud, what’s there not to like? Maybe you should resend it? Maybe you should have gone with the eggplant emoji to ease her into it? [Expletive]! No, you’re overreacting. The important thing is she’s seen your penis, and now she knows what you’re all about.

You’re a man with a penis. She wants a man without one? She can go have a general conversation about her thoughts and feelings that naturally builds until she gets to know the person and establishes a sexual comfort zone that would make sending naked pictures back and forth appropriate somewhere else. She’s a bitch anyway. Honestly I don’t even know why you waste time with these little immature hoes that can’t even – Wait. Yes. YES. She’s typing.

Tip 4: Back Pedal. Now:

Oh boy. How did we get here again? One minute you’re sending an innocent picture of your penis out of the goodness of your heart, and the next minute you’re trying to interpret what a single “lol” and nothing else means. So how do you salvage your reputation. Any mutual friends? Because now they know. They all know. They’re silently judging you, everyone is, but they’ll never tell. Just know that. Lucky for you, you can still turn this around with one simple trick: “Whoops. Sent the wrong pic haha.” Whew. Dodged a bullet there. You’re welcome.

Tip 5: Double Down:

So that didn’t work. She’s not responding anymore. Not about the dick pic; not about anything. She’s avoiding eye contact when you see her in public, and her friends are giving you weird looks when you run into them. There’s an unmistakable sense of creepiness about you now that you can’t seem to shake, and it only gets worse the more you think about it. You’re that guy now.

So what do you do? Let a friendship die because she can’t take a joke? (You’re calling it a joke now). No, real friends don’t do that. You have feelings you know, and clearly she doesn’t respect that. Bitch. Anyway. Now, you double down. Send her a dick pic every now and then to let her know how you’re doing. If she’s going to feel uncomfortable around you, at least regularly validate that feeling until she’s forced to publicly confront you about it. This way, everyone wins.

So that’s our guide.

Next up – Donovan Asks: Hey UGS, I’m a clerk at the tax office. How do I flirt over text when she gives me her number for the sole purpose of a business transaction?

Until then – carpe dick’em, gents.