Cover Letters are Like First Dates: 5 Ways to Behave

Heartache, self-doubt, and dozens of dead ends: job searching is a lot like dating. You put your best foot forward and then you sit by the phone. You lay awake at night, agonizing over what you should have said differently and wondering if there’s another candidate in the picture. You’re pretty sure this is The One…until you’re pretty sure it’s a pyramid scheme.

In the extended metaphor, cover letters are similar to first dates. Both are your first—and sometimes only—chance to make a good impression. Here are some rules that apply to both:

1. Respect Tradition

There’s a reason why bringing flowers, holding doors, and avoiding spinach-based dishes are good policy when it comes to first dates: these are tried and true pearls of wisdom, born of the trial and error of countless single people who have come before you. Likewise, your cover letter should follow some basic traditional conventions (yes, this rules out YouTube videos and origami swans).

Use business letter format (if you don’t know how, look it up), address what job you’re applying for and why you’re a good fit. Refer to your resume but don’t regurgitate it. Use a 12-point, reasonable font on a white sheet of paper. Lose the headshot. Last but absolutely not least, proofread several times before giving it to a friend to proofread again.

Sure, a cover letter printed on a chocolate bar wrapper that looks like Willy Wonka’s golden ticket will garner attention. But stellar writing skills and thoughtful content will earn you the right kind of attention.

2. Butter Them Up

Everyone appreciates a compliment, even employers. It’s always a good strategy to demonstrate to an organization that you’ve at least skimmed their website before applying to their open position. Take that one step further, and mention something specific that you admire about the company. Are you emboldened by their mission statement? Impressed with the profit margin? Encouraged by a commitment to customer service? Be genuine about it, but say so!

3. Meet Them More Than Halfway

Let’s say your date tells you that he’s a vegetarian, and a farm animal activist. Probably a bad idea to follow that up with your favorite turducken recipe.

It’s not true that every job ad has been pored over by the people that will decide who is hired (in fact, many are written by HR and may not accurately portray the position at all.) But, it’s generally the only thing applicants have to go on, which means that some part of your letter should address the skills and experience required. Does the ad mention the ability to manage multiple projects at once? Write about those three successful projects you worked on last year, and how they cultivated your big-picture vision as well as a keen eye for particulars.

This also means that each letter will have to be specific to the position for which you’re applying. But hey, you wouldn’t take that vegetarian to a Brazilian steakhouse, would you? Consideration counts.

4. Don’t Oversell Yourself

The inclination to list every skill you possess and every accomplishment you’re proud of is understandable; the job market breeds desperation. But desperation rarely attracts mates or job offers. Restraint, humility, and substance are qualities that people look for whether they’re seeking a spouse or a colleague.

What does that mean? Keep it to one page and ditch the details about your Pez dispenser collection, how much you can bench press, where you go to church, and how many kids you have.

5. Don’t Be Presumptuous

A lot of people end their cover letter by saying something like: “I will contact your office next week so that we can set up a time to speak about the position.” This is akin to ending a date by saying, “I think we’ve gotten along really well tonight. I will be coming upstairs when we get back to your apartment.” It’s a turnoff, but it’s also indicative of how well you handle boundaries and social norms.

You can’t force your way into an interview. Furthermore, hiring managers are busy people; interrupting their workday is not a winning tactic. They will not be impressed with your tenacity, but they will be annoyed with your presumption.

Another way in which the job search is like looking for love? That for almost all people, eventually—and thankfully—it will end.

Ashley Cook is a Community Employment Associate and Case Manager at a one-stop career center in the Midwest, where she provides services and support to people with employment needs. She is also a freelance writer. You can see more of her work at