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Recruiting a Boyfriend


The leaves are changing, the temperature is dropping and MBA1s are turning into Justin Timberlake (suits & ties). As I thought about the topic for this issue’s article, I keep thinking about how similar my current experience with OKCupid is to last years’ experience with recruiting. You may be wondering: How? I thought you’d never ask!


The Resume….is the Online Dating Profile:

This is your calling card: the summary of your entire life on a template form. When a page of bullet points or a list of random questions (award winners such as OKCupid’s “The six things I could never do without”) is all someone has to make a decision, you are faced with a challenge. How do you best represent yourself with such constraints? From the recruiting perspective, think of it like applying to a position in which you have no connections. You are the only link between yourself and the organization. There is no Stern network to tap into; no coffee chats you can conduct while chugging Sosnoff’s swill to get a competitive edge. You are going in blind. In this situation, your resume is the only thing that can speak for you and you want the words to be overwhelmingly positive. You agonize with your mentors in GMA, GFA or WTF to wordsmith each bullet point to death. Which action verb conveys that you’re the one who knocks, the Heisenberg of MBA students? Hours are spent on a paper that is skimmed at best. Don’t despair, online dating is even more notorious with quick judgments. OKCupid has the extra wrinkle of supplying photos…so many opportunities for potential disaster. At least someone will look at your professional resume before rejecting you. With OKCupid, your face could be enough. Frownie Brownie. Ideally, you want to select your best photo as your profile photo. Unlike your resume, your dating profile is heavily influenced by visual preferences. You can craft puns and witty sentences, but you cannot change your face. I’ve met people in person that must have applied some Photoshop witchcraft to their photos. This is a great strategy if you never plan to meet in person.  Can you imagine if resume drops required a headshot too? Ugh! I am continuously baffled by what users choose as their main profile picture.  I went through my recent “Visitors” tab and these are all OkCupid users that viewed my profile within the last week. I include this detail because I didn’t even need to seek out these gems, they found me! I’ve lined up the “resumes” and their stereotyped OKCupid buckets below. 

OKCupid Stereotype: “I’m Artistic because I have a DSLR” 

OKCupid Stereotype: “Serial Killer Next Door”

OKCupid Stereotype: “Secretly Married”

The Cover Letter…is the First Communication through OkCupid:

Your resume will likely be the same for many internship/job applications; however, you spend time tailoring your cover letter to show the targeted company your interest. You’ve acknowledge that you attended the corporate presentation, researched the company, and networked your ass off. A highly generic cover letter will likely not gain the same positive reception that a well-thought out one will. In the same spirit, messaging someone “hi” on OkCupid is obnoxious. You could send that message to a list of 10+ users within a minute. If you’re truly interested, make the person feel like s/he was your first choice, even if s/he is one of many. The right approach is to show that you’ve read the profile. I spent time writing it and it is nice to know that the person messaging me read it and is still interested. I’ve gone on enough dates with unqualified people. I defined “unqualified people” as men I had nothing in common with beyond physical attraction. Think of it like reading a job description (my profile says what I’m looking for) and then applying for that job (messaging me). I’m not sure how I feel about comparing myself to a job, but, I will for the sake of a metaphor. Unless you know something about the position, how could you possibly apply to it? If you start to panic when your other MBA1 classmates are applying to jobs you never heard of on Career Account, do not just apply for the sake of applying. If this new opportunity does sound exciting, invest some time to approach it right the first time. In both recruiting and dating, you get one first impression! Make it count. So you have perspective, check out some recent “cover letters” I’ve received below…


Applicant #1: The Creeper

September 19, 2013 Received at 2:51am

Hi. I am looking for fun tonight. We can meet at a public place I can pick you up.

Me: Meet in a public place at 2:51am? Really?


Applicant #2: The Question Asker

September 14, 2013 Received at 12:00am

Do you prefer Beagle puppies or Bengal kittens?

Me: Neither. I’m also assuming you cannot read since I mention pugs about 5x on my profile.


Applicant #3: The Knowledge Dropper

August 4, 2013 Received at 11:04pm

Hey, you look like a HIMYM type of girl

Me: Thanks? I had to Google that the acronym stood for “How I Met Your Mother” and I still don’t know what that means.


I’d much prefer getting significantly fewer “applications” if the candidates were well-qualified. My experience to date has been a complete free-for-all of messaging. In order to preserve whatever level of respectability we are aiming for in this student paper, I won’t include the lewd messages I get constantly. To give you an idea of the level of depravity, think 50 Shades of Grey meets Law and Order: SVU meets Close Encounters of the Third Kind. You may be thinking: that is seriously f-ed up! Well, you’d be 100% correct. Since I’ve joined OkCupid, I’ve received such a colorful range of messages that it takes a lot to really make me jump. But boy, do I still jump sometimes!


First Round Interview…is the First Date

Congratulations! You spent a significant amount of your precious time on that resume/profile and cover letter/message and now you have something to celebrate! You’ve managed to get to the first round/first date. In both situations, you’re freaking out. The stakes are even higher now. What should you wear? Professionally, you want to be conservative but still demonstrate your personality. Add some creative flair to that pantsuit ladies and gents. Personally, your first date outfit straddles the line of revelation: you want to reveal your best assets, without literally showing your assets. This is generally a good rule to follow. Your outfit communicates your intentions. If you’re nearly falling out of your shirt at the beginning of the date, you will likely have no shirt on at the end of it. True story.


A key detail of the first interview is location. Will you be in the small rooms in OCD that are incredibly warm or will you be on the company’s turf? While you cannot control where the first interview occurs, you can control how you prepare. Tips: Show up early (add on 15 additional early minutes because the subway will most definitely break down), bring mints and get business card information. In dating, the location of the first date is much more in your control. If you are suggesting a location, pick a place with these qualities: a drink selection you will both enjoy (a full-bar is a better bet than a wine bar), an atmosphere for conversation (avoid yelling on a first date, that is weird), and a location that isn’t incredibly annoying for either of you (if you’re East Side and he’s West Side, pick somewhere in the middle or by a major subway line). I’ve listed some fun suggestions below that meet the first two criteria (selection and atmosphere). If you’d like more suggestions, please Tweet me @personalitini!

Beer Focus/Casual: The Ginger Man (Midtown West) / 11 East 36th Street

Awesome Happy Hour/More Upscale: Pranna (Flatiron) / 79 Madison Avenue

Speakeasy/Upscale: The Dead Rabbit (Financial District) / 30 Water Street


Ok. Location set! Now you need to meet in person! The first time you meet someone in person is incredibly stressful. Both interviews and first dates make you face the fear of the proper greeting. With an interview, you want your handshake to be firm, confident and not sweaty. With a date, you have so many other things to worry about.  Will one person go in for a hug and the other reciprocate with a super-serious handshake? I get incredibly apprehensive about this. I think men can be hesitant of making this decision, so I go in for a hug pretty early. Note: If my date looks like a different person than his profile, I react differently, potentially by exiting as soon as possible.


At the conclusion of the interview, you know exactly what to do. You craft the perfect thank you (after freaking out about the exact sentence structure for an hour or two) and click send. You did your best and it is out of your hands. When you’re done with the first date, oh my, who does what?! At this point, you both have each other’s numbers. So, who calls/texts/emails/smoke signals who? It is unclear if the man should make the first move. As a woman, I think it is engrained in my gender to expect men to act first if interested (“I mean, if he’s interested, he’ll like totally text me, right?”). In my opinion, there is so much bad advice out there that men are likely incredibly overwhelmed. If I’m interested in participating in the “second round interview,” I make it incredibly clear. I will send a text like this: “[Name] thank you for a great night! It was a pleasure meeting you and I’d love to do it again. Have a good one.” I typically send this the next day, so it doesn’t come across as stalkerish (he doesn’t know I’ve been obsessing over it all night). If I hear back and he wants to make plans, I’m thrilled. If I don’t hear back, I also have an answer. Knowledge is power. I’d like to move on as soon as possible, so if someone is not interested, let’s both get on with our lives.  

Second Round Interview…is the Second Date

Now, the stakes are even higher. You’ve both made it past each other’s first round of qualifiers. As a job applicant, you’ve impressed your interviewer and distinguished yourself from the candidate pool. All of your hard work has paid off! You know going into this next interview that all of your competition in this next round has also made it through all the hurdles. The promise of the next step is both exciting and terrifying. You’re so close to something that could be wonderful but you don’t yet have it. In my OKCupid dating experience, this is where I struggle the most. I’m great at first dates! From my perspective, I feel like many of my first dates are awesome. Even if I didn’t have physical chemistry with my dates, I manage to have great conversations the majority of the time. I may not want to make out with my date, but I would be happy making pleasant conversation. What confuses me is that I never hear from many of these people again. It makes me wonder if I’m doing something that is an incredible turn-off. My photos are all recent, so hopefully it isn’t a matter of appearance. This is a topic I will explore in my next article. As Shawn McClain inquired, this paper, unfortunately, isn’t called The Personalitini…at least not, yet. So, I need to keep an eye on word count! I digress! If you find yourself in a second round/date situation, this is decision time. You each like each other enough to see each other again. The setting will likely be different. For many companies, you will be invited to a Super Day. As for your date, this can be seen as the Super Date. Instead of drinks, maybe an actual meal will be involved. The setting will likely be nicer and the time spent together will likely be longer. Do you need inspiration for your second date location? See below for some spots that are fun for both guys and gals.

Casual New American ($$): Almond (Flatiron) / 12 E 22nd St

Asian Inspiration ($$): Mission Chinese Food (Lower East Side) / 154 Orchard St

Trendy Tapas/Cocktails ($$$): Beauty & Essex (Lower East Side) / 146 Essex St


The Offer…is a Relationship

Congratulations! It is an incredible feeling to have an internship or full-time offer in your hands! You aced the resume, cover letter and both interviews. You deserve it! It is hard for me to comment on this part from the dating perspective. When reviewing my relationship history, I have not had many long-term relationships (I consider this over a year). Unlike your professional search, your past career achievements, awards or other recognitions do not translate into chemistry with a romantic match. I am incredibly happy to have found my dream career and company. I become frustrated when I haven’t realized this same success in a romantic relationship. I’m using my MBA2 year as a period of reflection. Through this column, I hope you will continue to follow along on my journey of self-discovery and securing an “offer” of the heart.


Until next time,