I haven’t been single for almost 5 years and I’m pretty happy about it. I love my partner, we have a nice life together, support each other and in general, he’s my best friend. It’s not that I was unhappy being single before, it’s just the whole dating process was so…tiring.

I would go out on several fun dates, paint the town red and have fun. Then those pesky feelings would get in the way.

Does he like me?

Is he going to call me back?

OMG, I texted him three times, am I needy?

I would analyze every bit of conversation with my girlfriends to detect any revealing information.  I would go on and on about everything and wonder, what’s the next step.

Online dating was the worst. Pic for pic? Ugh, I’ll be happy if I never see that phrase again.  I remember falling in love with several online ads, imagining what awesome stranger was on the other side. I’d send my cute photo, out into the unknown. Of course, he’ll respond, right? I sent a witty, intellectually stimulating response with a cute photo.


crickets chirp

The feeling of shame and loneliness that follows a no-response-after-photo, is so incredibly awful. You realize how shallow people really are. If you don’t fit their ‘idea’ of who they thought you were, it’s over. And you don’t get a say in it.

I feel like looking for a job, and the interviewing process is a lot like dating. It sucks. Except with interviews, there are no free drinks, dinners and the power is definitely on the side of the interviewer.

I’ve had about 30 interviews in the past year and a half and have learned so much from this crazy process.  Many of those interviews went really well, but clearly they didn’t work out, mostly because they ended up hiring someone internally or went with someone with more experience.

The most frustrating part so far has been when an interview goes really really well. I DO get a second interview, maybe even a third, or fourth. And then I wait….and then I hear nothing. I’m thinking of the interview I had 2.5 weeks ago. It was a THREE HOUR interview, with three different people, with incredibly difficult situational questions. All of my friends agreed they would have no clue how to answer the questions these people threw at me, but I responded from my experiences in my previous job, with grace and professionalism. I felt like I was talking to my friends…it was comfortable, nice and we clicked. They told me they were going to get back to me by the end of the week, which was a week and half ago already. At first I was doing pretty well with writing the whole situation off after I didn’t hear from them.  Then, I started getting frustrated. I spent 4 hours (1st and 2nd interview) of my life getting grilled and I can’t even get a formal rejection?

Then the crazy speak starts:

It went so well. I did everything right. Did I imagine that?

We clicked, I thought it was a real connection. Is there someone else?

Some people have tried to be positive and say ‘sometimes these things take longer than expected’. But to be frank, I’m over waiting on this one.  I even followed up with an email late last week and haven’t heard a peep. After all these interviews, putting myself out there and jumping through hoops, I am so over it. The thing is, when I was tired of going on bad dates, or getting rejected, I stopped dating. I didn’t need to date, it was a means to an end and something to fill the time. However, I can’t stop looking for a job. If I am out of the game, I lose. If I stop, I definitely won’t get a job. I don’t know what else to do to revitalize my search efforts. I don’t know the meaning of ‘stay positive’ or ‘it will work out’. I know I sound like a negative nancy but it’s how I feel.

It’s nice to know that I have gotten so many interviews and that I’m getting noticed. But I am not sure if the probability of me getting a job goes up with more interviews. I just need that one good interview for the right job, and I’m done. Just like dating, you need just one good date to form a relationship.

I was talking to my friend about my frustrations and my comparison of looking for a job to dating. He said, ‘well if you think it’s like dating, then a job will come when you least expect it’. Ugh. He’s so right. I found my partner when I threw in the towel and was done going on dates. At the time I was bitter, but I agreed to go on one more date, a blind date at that, that was set up by my friend…and almost 5 years later we are still together.

I hope I can have an awesome story like that about my next career. In the meantime, I will keep on trying (to preserve my sanity).  Any tips on keeping yourself motivated when you just want to give up?


Melanie is a freelance writer currently living in Portland, Oregon. She is passionate about education, financial literacy, and empowering people to take control of their finances. She writes about breaking up with debt, freelancing, and side hustle adventures at DearDebt.com.

Currently she puts more than 50% of her income towards debt, while living a frugal, fun life. In addition to her love of personal finance, art and music, she is also a karaoke master. Follow the adventure @DearDebtBlog.

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32 responses to “Why looking for a job sucks as much as dating”

  1. It’s tough. I usually don’t even get job interviews because I’ve given up at trying to find a full-time career and I seek out part-time jobs where my resume/application probably winds up floating around in a pool of hundreds, maybe thousands. It sucks. Sometimes, it’s like playing the lottery. I guess you just gotta keep at it, good luck! Honestly the people you know, networking, seems like the way to go. When I was in college my roommate and I applied for the same job. He had a friend who worked there and despite failing the assessment part of the application process, he was hired because of the recommendation. You’re in the Portland area, yes? What kind of work are you looking for? I have several friends, entrepreneurs, who might have/know of positions available.

    • doordebt says:

      Why have you given up on a full time career? I’m trying to utilize my network, keep hustling and keep trying. Something I am trying is applying for jobs if I have at least 50% of the qualifications….my old self would never do that, but someone suggested it. What’s the worst that could happen? They delete your email. I have one more interview today, for a job that I wouldn’t have applied for if it wasn’t for this rule. So that is good! I am looking for work in the non-profit, arts, education sectors, but can be flexible.

      • My education at a for-profit school has proven to be subpar (and the biggest mistake of my life). I tried for a year and a half but most of the jobs in my field are freelance and the jobs are sparse considering the amount of people who major in the arts. Including my BFA degree on my resume for jobs not in the art field get me nowhere unless they’re part time, usually minimum wage.

  2. I understand your struggle and I feel bad for you. I won’t tell you that things are going to work out in the end, because that’s not really what you need to hear. You’ve already heard that and advice like that is pretty much a way of saying “I care, but not enough to help”. I recommended before that you read “Your Money or Your Life”. I really think it would help with your struggle. It’s an easy, quick read. It’s fun, and life-changing. If you can’t afford to buy a new book, go to the library.

    I realy hope this advice can help you out. Life is full of uncertainties, and employment shouldn’t have to be one of them.

    • doordebt says:

      THANK YOU! It’s refreshing to hear that. Seriously, I want to go to the library and get that book this weekend! I promise I am taking it to heart 🙂 Especially if it can help my overall malaise.

  3. I don’t really have advice, but I do have a lot of sympathy. What is up with place where you interview and when you follow up, they don’t have any kind of response whatsoever. Especially one where it was such a long interview. Even something as simple as, “we’ve gone with someone else” or “we are still reviewing candidates.” At least it’s something. Back in the day, if I even got an interview I usually got the job offer, but something happened now with me freelancing. I have yet to get a job offer from someone I interviewed with. Not sure if it’s the “times” we live in or it’s me. I don’t necessarily think you should stop looking like when you were dating, but work in expectations of others, pace yourself, and keep yourself busy and occupied do you’re not always thinking of what the interviewers are currently doing.

    • doordebt says:

      I think it has to be the times. For my last awesome job, I looked back in my files and looked at my cover letter and resume….it sucked! I was only 22 and didn’t really know what I was doing, and ended up landing an awesome job. Now, I have way more experience, know how to actually write a cover letter and resume, it gets me interviews…but then…..? I think the key is to keep doing what I want to be doing, whether someone is paying me or not, and continue to find ways to make money.

  4. Man, a third or fourth hours-long interview seems really ridiculous – sorry to hear that you had to go through that. I don’t have a lot of advice, but coming from a side where we’ve had turnover in the past, sometimes hiring someone is a LOT of bureaucracy with HR (and even if you have someone in mind, you can’t give anyone updates since the official offer has to come from them!). That being said, I think it would be the kind thing to do to at least give you a courtesy follow-up email, even if it’s to say that they’re still making decisions. I really like your correlation with dating and job hunting, and agree with your friend that maybe it will come around when you least expect it. I will think positive thoughts for you!!

    • doordebt says:

      Yeah, I am SO familiar with bureaucratic bs. It could def be that. A courtesy is just that I guess….a courtesy, a non-necessity. I have one more interview today, then will continue applying/hustling!

  5. I love your writing! It’s so relatable. I had the same issue once; I had 4 interviews with the same company and they made it really seem like they were going to hire me, and then I never heard back from them even after the follow up. Job searching is just so annoying. Keep your head up!

    • doordebt says:

      Thanks so much for the compliment! That is awesome. I once had 4 interviews with a company (9 hours of time!) and I thought it was a done deal too– then never heard from them again! The ED said she loved me. I don’t understand. Thanks for taking the time to read and comment and welcome 🙂

  6. This is a great analogy. Never thought of it like this before. At least with dating, there are other women out there but jobs are tough to come by. I enjoyed this article.

  7. Ugh I can’t decide which one I dislike more, looking for a job or dating! I don’t know if they have this in the US but have you thought of looking for work through a recruitment agency? Basically you send your cover letter and resume to them, they do an interview with you and test your skills, and then the recruiters look for jobs applicable to your skills. This is what I did when I was working at the bank and didn’t have the time to look for another job. Either way, i agree with Anna and your friend, the right job will come along when you least expect it. Good luck lady! *hugs*

    • doordebt says:

      I think once my contract is done in a few weeks, I’ll look into a temp agency and keep on with my hustlin’ ways. Thanks for your support! 🙂

  8. You’re right, it is like dating! Ugh I hate interviews too and I hate when they say they’ll get back to you and don’t. I always follow up with an email so I don’t go crazy but still it’s so annoying!

    • doordebt says:

      Right? It is sooooooo annoying, especially when you follow up. Interviewing is like dating…you are essentially selling yourself, trying to make that connection and hoping the other person likes you! It’s exhausting.

  9. Ugg, I feel your pain. I had a really hard time finding my first professional job after I finished grad school. I wrote a post a few months ago titled, Date the Boss to Get Ahead http://www.studentdebtsurvivor.com/date-the-boss-to-get-ahead/ describing the similarities between dating and interviewing. It’s a painful process sometimes. Hang in there!

  10. Don’t feel discouraged. I was in a similar situation when I graduated college in 09. The economy was in shambles and I went on about 50 interviews but didn’t get hired. I waited 7 months to find an entry level position. Almost 3 years later I have gotten salary increases and have been promoted a couple of times already. Just hang in there and persevere and you will find what you are looking for.

  11. […] Why Looking for a Job Sucks as Much as Dating One of my friends just finished a two month long interview process (and got the job!), so I could definitely sympathize on this one. […]

  12. Jessie says:

    Loved your comparison of finding a job to dating! I recently liked interviewing to “The Bachelor” as dumb as that show is…all these other candidates but you think your date is going great until you’re without a rose and packing your bags 🙂
    But really, hang in there with the search. Totally sucks and you have every right to complain, the market in Portland is awful.

    • doordebt says:

      Yes, it DOES feel like the bachelor. No rose for me, haha. Yes, the market in pdx is pretty brutal, but I’m hanging in there and will keep at it.

  13. Whenever people talk about how to approach job searching like dating, I want to reach through the monitor and shake them, screaming, “DO YOU KNOW HOW MUCH I HATED THE DATING SCENE!?!”

  14. LivingDebtFreeRocks! (@LivingDFRocks) says:

    I haven’t had to interview since 2004 and I would dread it if I had to start that process. You’re right, job interviews are exactly like dating. Thank God I found someone years ago who I’m perfectly happy with. Keep us posted in your job search efforts and I really hope you land something great soon!

  15. easy123 says:

    Hey doordebt,
    Its been over a year now, hows it going? Found this article and you are completely right! Im in this same situation right now. I don’t know what field you’re in but its worse for software developers. A lot of times they give you coding assignments that take 4-6 hours to complete only to find out they hired someone else and didnt even look at it or they didn’t like your code.

  16. Clair says:

    You think looking for a job sucks at your young age? Try looking for a job when you got laid off after 13 years, are over 60, you’re single with no partner to help you and have to work because you don’t have enough for retirement. (My fault I know) I’m very up to date with correct type job description for today’s world, my LinkedIn profile is star status and I network a lot. I have 30 years of real world, hard life experience and I’m told “your age will be a problem” and “the majority of the job force today is mellinals. Enjoy being young enough to have the luxury to get that job. ADVICE: save, save, save for retirement. You’ll be my age befor you know it.

    • Melanie says:

      Oh, Clair. I’m so sorry to hear this. I hate that there’s ageism out there 🙁 This is a good lesson for younger folks. I hope things get better for you!

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