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I met "Jeff" at a press event. I immediately noticed how cute he was when he asked for my name at the lunch, but there was little more than flirty eye contact. As we all shuffled into the restaurant, I was thrilled to realize that he was in the assigned seat directly next to me.

We chatted during lunch, a little about our respective positions, the city and the usual getting-to-know-you topics. On my way out, I handed him my card with a big smile and said, "I forgot to give you my card before. Here's all of my information."

The next day, I was pleasantly surprised to receive a message alert at work from him. He sent me his deets and added, "So nice talking with you yesterday. I had the pleasure of sitting next to you!"

Click here for what happened next -- and to give Jennifer advice on how to proceed.

The Most Annoying Co-Workers

    Insistent Instant Messenger: No matter how much time or miscommunication could be spared by talking face-to-face, this person insists on talking virtually, via IM or email. If they're a superior and you're not online, they send you an email to ask where you are (meanwhile you're at your desk, ten feet away).

    Cycle Sister: This is a person you're not particularly fond of, but for whatever cosmically twisted reason, your daily routine is synched up -- you walk into work at the same time, and from there, you see your Cycle Sister in the bathroom, on your smoke break, at the vending machine, and on the way out. Even if you do like this person alright, the sheer coincidence makes things creepy and awkward.

    Mr. Flibble, Flickr

    The Get-a-Lifer: This person asks you out to post-work drinks on a regular basis, despite the fact that you always decline. And the one time you went to a party at their house, it ended up being the two of you playing Taboo. The Get-a-Lifer is often the same person who plans meetings at 6 p.m. on Fridays, not realizing that everyone else goes out with their friends on the weekend.

    bealluc, Flickr

    Listserv Leech: If someone has taken this person's lunch out of the fridge, the entire staff will be notified via the staff listserv, which everyone else uses exclusively for professional communication. Alternately, this person may use the listserv to let everyone know about the lack of toilet paper in the bathroom, a party they're throwing, or to ask who took that package off their desk.

    Angry Typist: The Angry Typist pounds on her keyboard with the vigor of someone hitting their ex-boyfriend. The violent clacking leads to many misunderstandings, as this person is often unaware of their problem and is not actually pissed.

    .faramarz, Flickr

    The Toilet Mouth: You're on the pot midstream (or worse) when the Toilet Mouth strikes up a conversation. This person also likes to chatter at the sink for before and after they go, giving no one in the bathroom privacy to do their business.

    Megan *, Flickr

    Monday Manic: The coffee hasn't hit your bloodstream yet, and the Monday Manic is flittering about, imbued with an unnatural amount of energy and optimism. They're telling stories about how freaking great their weekend was and so stoked about the work they get to do that day.

    Old News Hound: OMG, did you hear that Lindsay Lohan is dating a girl!? The Old News Hound is always the last to know about everything, but the first to belt out at a stale headline at full-volume to their surrounding coworkers.

    Rash Revealer:This person has no shame getting on the phone with their doctor, their spouse, their aunt, or their mom to discuss a rash, a yeast infection, and any other personal bodily defect or medical issue.

    maydaFUNKbewithu!, Flickr

    The Chit-Chat Blaster: If this person catches you in the break room or on your way out of the bathroom, you're done for a half an hour later they're still yammering away about the paint samples they're considering for the livingroom, the deli they ate at for lunch, the meeting the boss called earlier, the diet they're on. The Chit-Chat Blaster also doesn't notice you inching away, and generally lack the ability to pick up social cues.



I wrote back something short and sweet and added at the end, "I hope to see you again soon!" He wrote back "I hope to see you again soon too." I groaned.

Flirting or Networking?
This back-and-forth was ridiculous. We were tip-toeing around each other, and I was still kind of confused. It's not like I met him at a bar -- then I'd know he was interested if he e-mailed me. But since I met him an industry deal, maybe he's just being polite -- or networking. Gaah!

So now I'm wondering if I should just bite the bullet and ask him out. How (in)appropriate is it really to ask someone out via work e-mail if that's the only contact info you have?



Jennifer S blogs about relationships and sex for Lemondrop.

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