Ask TSJ: I Want to Ask My Receptionist Out

Life is hard. It seems like every new day brings a new question that, try as you might, you’re just unable to find an answer for. The Smoking Jacket understands this, and we’re here to help. Media sensation Tracy Pendergast and TSJ’s brand-new editor, Melissa Bull, set aside some time in their busy schedules to answer your questions in a feature we’ve cleverly named “Ask TSJ.”

This week’s incredible question comes from a TSJ reader named David.

Q: I’VE BEEN INTERESTED IN THE RECEPTIONIST AT MY OFFICE FOR MONTHS. I REALLY WANT TO ASK HER OUT, BUT I DON’T WANT TO HAVE TO SEE HER EVERY DAY IF SHE SAYS NO. I HAVEN’T TALKED TO HER LONG ENOUGH TO EVEN KNOW IF SHE’S SINGLE. WHAT SHOULD I DO?

- DAVID

 

TRACY PENDERGAST: David, I can’t let you avoid this any longer. You have made something very sweet and innocent into the sixth installment of Final Destination. You need to talk to her!

I don’t know what kind of office you work at, but in my days as a temp, I was a receptionist for a number of businesses. If her days are anything like mine were, she is sitting there praying that someone even notices she exists.

If you’re nervous to ask her out right off the bat that’s ok, but let’s get some dialogue going. Next time you step out to grab a coffee, swing by her desk and offer to grab one for her too. Not a coffee drinker? Tough luck dude, this is how office shit goes. Once you’ve done this a couple of times you need to just step up to the plate and ask her out. Tell her exactly like you told me— that you’ve wanted to ask her out for months but don’t want to seem like a creep. Keep it short and sweet. Don’t go into specifics about what kind of date you have in mind, be vague. If you offer a chick a horse and carriage ride or something you’ve obviously been thinking about for days, that can get awkward.

She may say no, but that’s okay—don’t panic! You manned up, and you should feel like king of the office for that alone. The great thing about women is, even when we say no,we’re still flattered. You have still made her day. Continue to offer her that occasional coffee so she knows you’re not phased by her punk ass, and set your sights on someone else.

This is a new year, and this year you need to take some risks, David! I have a good feeling about this one…

 

MELISSA BULL: Talk to the lady, but nix the grand emo reveal is my two cents, David. The whole ‘I’ve been thinking about you all this time’ shtick could creep a girl out. It would def give me the heebeejeebs. So this is what you do. Set up some office hangs. Say to the receptionist lady: ‘A bunch of us are getting beers at the pub after work, you should come.’ Then get the show on the road and make it happen— just make sure at least one other person tags along. Like a married person would be ideal. Easy enough, right.

When you’re out, pull up a chair beside receptionist chic. Not cloyingingly near, but close enough you can get some one-on-one going on.  Otherwise there’s no point to this whole excursion, is there. You’ll make some eye contact. She’ll get cute and tipsy. You’ll ask her about her job, because that’s the first easy question. But here’s the thing: Her job is lame. So probably she’s doing cool stuff on the side. Ask her about that. Bonus: There might be something she does on her time off you’ll be invited to tag along to. Like maybe she loves metal bands or something. Equals continued access to receptionist lady.

The question that cuts to the quick: What did you do on the weekend? That’ll tell you whether she’s single or not. If she says I partied with my boyfriend, then you’ve got your honorable discharge.  If her answer is: I hung out with my big sister Trudy, maybe next time you go for beers without married dude from I.T.

Either way, you went drinking with the hot receptionist. Win-win, my friend.


Tracy Pendergast is a writer, model, singer, television personality and former Navy Seal. We might be lying about one of those facts. Check out her
official website or follow her on Facebook, or on Twitter @tracypendergast to find out which one.

Melissa Bull is the new editor of The Smoking Jacket.

Got a question for Melissa and Tracy? Click here and fire away. If we use it, your life will improve immediately.

 

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