Single Woman Chronicles #1 – Online Dating Hope and Rejection

This post marks the start of an ongoing series that I am calling the Single Woman Chronicles. This series will appear from time to time and cover the ‘Single Woman’ part of Double Debt Single Woman. Enjoy!


I am now in a new city with a new job, and with new hope for curing my singleton problem. I’m still in a steep learning curve at my main (office) job, while getting the hang of my second (online) job. So, in short, I’m busy and tired all the time. Working so much keeps me distracted from the fact that I am very, very single.

I’ve been here for a few months now and have yet to make any friends or meet anyone special. I know, three whole months! I’m bored and boring. After all, only boring people get bored, right?  I decided to reactivate an old profile on one of the online dating sites. Profile content – no problem, settings – no problem, photos – problem. I didn’t have any recent pictures.

I have no friends yet to photograph me in cool places, doing cool things. Fine, I decided to put up selfies. (By the way, I really hate the word ‘selfie’.)  I thought about getting professional pics, but shot the idea down. I did that before, when I first opened the account a few years ago. I had my hair and makeup professionally done. I even hired a photographer. The pictures were beautiful. I looked great! I even got some guys sending me winks and emails. Unfortunately, I didn’t look like the pictures on a day-to-day basis. Who could keep that look up?! This hit home one day when I spotted one of the guys who had messaged me in a local grocery store. I was not looking hot. I tried to hide from him, but I could tell that he’d recognized me too.  He never approached me and I don’t blame him. I got out of the store with my purchases as quickly as I could. I took those photos down soon afterwards. That online dating stint was a total failure.  I learned my lesson about putting up ‘glamour shots’.


LoL. Remember ‘Glamour Shots’?

So, back to present day. I want my pics to be natural and real – the real me. Now, most of us think of ourselves as relatively attractive – not models, but not trolls either. Despite being more of a plain jane, I think I’m quite cute. My iPhone camera, unfortunately, does not agree. After taking dozens of selfies, the camera roll reveals shot after shot of a distorted, blemished, and haggard face. OMG! WTH?!  Where is the cute chick I see in my mirror?  Gizmodo has a great article about why we look different in photos than we do in the mirror. (Yes, I had to look this up!)


[Image credit:]

In desperation, I picked the least horrible one in the bunch and threw it up on the site. (Sorry for that visual.) Yes, only one. It was a closeup shot of my face sans makeup, which I usually don’t wear, taken in the bathroom mirror. Yeah, I know, but bathroom mirrors have the best lighting.  I did a bunch of searches for potential matches and sent out about 10 personally crafted emails. As a woman of a certain age who is not classically beautiful I have learned that I have to be proactive when it comes to trying to meet anyone online. And I waited.

A few hours later, I got two responses! Woot! Upon opening, one said, in a short but sweet way, thanks but no thanks. Ok, fine. The other one was not scathing per se, but was very detailed in a judgmental way about why I was not a match for this particular individual. Ouch. This second rejection rocked me. Combine this with the fact that as of the following day, the person that I most wanted to hear back from (omg, major crush!) had read my message, but not replied. I felt so sad and rejected that I hid my profile. Within two days of getting online, I was retreating like a wounded puppy. I needed time out to heal psychologically. With that rude awakening, I realized that I had been out of online dating for a long time. I forgot about how much of a thick skin you have to have.

Not interested

A week later I reactivated my account with a thicker skin.  My profile has been back up for a few days now. I continue to send out a few messages per day. I have yet to receive any messages. Note: I am not messaging models, actors, or tycoons here. I am very realistic about who I message. These are regular looking people with regular lives, like me. Most of them have profiles that show that no one has contacted them all week. They read my personalized message, then… crickets. I know this is par for the course for online dating, but damn. They’d rather continue to be alone than talk to me. Ouch.


LoL. I have to laugh about it. I still hold out hope that something may come of it. In the meantime, I have to make more of an effort to get out and take a class or join a few clubs — oh, and find the number of a good photographer.


“Debtor’s prison is real, and opportunity cost is a bitch.” (DDSW)


  1. unchainedsoul · November 8, 2013

    Oh man! Ouch! I totally know where you are coming from. I have those glamour shots too and let me tell you, since they are only head shots, I had a guy tell me, you look skinnier in your pictures than you are in real life! Ouch, I know you don’t want me, but to attack my fatness! UGH! I will give the dating game another try someday, right now I am not thick skinned enough lol. Good luck on your search!


  2. Amanda @ My Life, I Guess · November 8, 2013

    I rejoined a free online dating site about 6 weeks ago, admittedly just looking for an “ego boost” after a relationship ended. My profile picture was from a wedding photo-booth where I had fake teeth and big pink guitar glasses. I picked it because it still kept me “anonymous” – but I got a WHOLE lot of response from it. I suspect because it was an ice-breaker in itself?

    My two cents would be to try something like that? Instead of having a photo of just your face, purposely try an “icebreaker” picture – you participating in an activity or hobby you like, or a travel pic, etc.

    More and more couples I know met online these days, so there’s gotta be something to it, right? Best of luck!


  3. czanclus · May 3, 2016

    You wrote this piece a long time ago when I didn’t “know” you, so I realize my comment is dated, but either way I wanted to let you know that I’m rooting for you in this department as much as in the financial department. If I were a guy (or a gay woman) in the business of dating/partnering up, I would definitely consider someone with traits such as yours as top choice because of your tenacity and ability to look on the bright side of things even when a normal person would scream and give up – all the while fighting out of your rut with only yourself to lean on.

    The people that have it good are at best aware of how good they have it in the abstract – and because, you know, it paints them as more magnanimous if not only are they well off money-wise, but they UNDERSTAND and CARE about the plight of the less fortunate. They are not selfish, ruthless psychopaths like all the other $$ hoarders out there. And it is way too easy to ascribe one’s fortunes to a just meritocracy – ‘why, I worked HARD and applied my EXCEPTIONAL TALENTS most persistently – which is the sole reason why I got here.’ – when in reality, they 999/1000 just had better luck and opportunities at all junctions.

    Anyway, never give up believing in your worth. If a guy deserving of a fighter princess warrior that you are is out there, he will find you. I, in my old-age cynicism, cannot however attest to the veracity of the first statement. :-[


    • doubledebtsinglewoman · May 3, 2016

      Thank you. Yes. Going through our own money problems oftentimes makes us more observant of the financial behaviors of potential partners. I don’t get any practice making observations myself, but I imagine that it is the case for single ladies who actually have suitors. 🙂

      LOL at your last sentence. 🙂


  4. Kira · October 11, 2021

    This was lovely to readd


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