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Ask Anna: Has dating coworkers changed in the remote-work era? Plus, how do guys send sexy photos?

I’m crushing on a coworker, and wondering if the workplace rules about not shitting where you work still apply in a COVID-era, remote environment? He and I don’t interact hardly ever at work––we’re in different departments––so even if we did date and break up, the repercussions would likely be minimal. So…should I go for it?––Work Opportunity Reaches Kissing

Dear WORK,

That is an interesting question. In a world where many jobs are going fully (or largely) remote, do the rules about dating coworkers need to change? My answer is yes. And no. 

Why yes? As you say, in a remote world, our interactions with coworkers largely occur online now and not off. This reduces your chances of awkward run-ins with any exes, past or future.

And, as you don’t work in the same departments (and don’t plan on it; i.e., you won’t be transferred to the same team or reporting structure through a re-org or promotion), then you’re likely fine to pursue something with your crush.

Why no? Just because a lot of our work interactions occur over Zoom now doesn’t make work breakups any less shitty or potentially awkward (even if the circumstances are lessened or different). If nothing else, simply being at work will remind you of your (at this point hypothetical) ex, even if you’re not physically running into each other at the shared office toaster on Bagel Wednesdays. 

Whether remote or not, my advice around dating coworkers is always a risk vs reward question. Do the rewards of asking out your crush outweigh the potential risks of a fallout? If yes, then invite him out for an IPA and some queso dip. If not, then, well, there are plenty of other fish in the Meta sea. (I’m guessing! I don’t swim in virtual seas.)

I (24M) started dating my gf (23F) about six weeks ago. As we’ve gotten to know each other more, she’s started to send me sexy pics over text. I usually send her back some abs pics, but I want to up my sexting game here! What should I send her? She says she doesn’t want dick pics LOL.––Showing Myself Shirtless

Dear SMS, 

I love that you’re getting creative about your sexts! It’s refreshing. So, first off, you don’t always have to send a photo back after you receive one, though the gesture is often appreciated. Other pics to consider, aside from abs, include:

Suggestive pics. A thumb hooked in boxers or briefs, post-shower pics with steamy mirrors and strategic swipes, tangled in the sheets, etc. Also, while butt cleave is often derided (hello, plumber’s crack), don’t outright discount it! Some women go wild for buns. No matter the pose, make sure to look at the camera with your most intense bedroom eyes. 

A striptease. A series of photos where you lose one piece of clothing at a time. Bonus if the text includes what you wish you were doing with your gf at that moment. 

Overlooked sexy body parts pics. Maybe you have dreamy eyes, ripped forearms, or devastatingly handsome knees. Don’t be afraid to send less typically erotic body pics, especially if you’ve been complimented on said parts.  

The direct approach. Ask your lady what her favorite body parts of yours are and then send her pics accordingly. Tell her your favorites of hers in return.

When all else fails, google. The internet, it doth provide. Find a Tumblr/subreddit/photo blog that posts erotic male photography, and then copy your favorite poses/angles/lighting.

Anna Pulley is a syndicated Tribune Content Agency columnist answering reader questions about love, sex and dating. Send your questions via email (anonymity guaranteed) to redeyedating@gmail.com, sign up for her infrequent (yet amazing) newsletter, or check out her books

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