Do You Date While You’re In Transition?

Name: John
Age: 45
State: NY
Question: I have worked for the same large company for over 20 years. A year and a half ago, I sustained a neck injury which prevented me from working. Fortunately, the company had a policy where longer term employees can be on fully paid medical leave for up to 2 years.

I am now fully recovered from my injury but due to the red tape between my company and the insurance company, it may be a couple of more months until I am actually working again.

During my recovery, I had no interest in dating but now that I am fine again, I am ready, willing and able to date. This will be the first time I will try online dating.

My question now becomes, will that story be a turn off to perspective women? Should I not mention this at all and just act like I am working? It would be quite easy to do and would solve my dilemma. But I wouldn’t feel comfortable about lying or misrepresenting myself.

The most conservative option is to just wait until I am at work again and this won’t even be an issue. Is it unreasonable to want to begin now? I see some ladies that I would like to contact and am afraid they wont be there when I am actually at work a few months from now. Your thoughts?


I have to say that I’m torn on this. I think your success depends on how you present the situation. You’re not out of work. You’re waiting for the green light to go back to work. So you have the desire to work. That’s what really matters.

I think what might get in your way is if you hide your situation in some way. Here’s an example of what I mean.

I once met a guy online who said he lived in Manhattan. His profile said that he had just moved here for work. When we were making plans to meet up, I asked him in what part of town he lived. That’s when the real story came to light. He was staying with a friend while he looked for a place. He had been there for almost 6 months. Now, here’s my thought process:

*Who comes to NYC to work without a place to live?

*Why hasn’t he been able to find a place to live in 6 months?

The conclusion I came up with was that he likely wasn’t working steadily and couldn’t afford to get a place yet. Or that he was here on a whim and likely might leave in the not too distant future. In any case, I decided not to meet up with him. Oddly, he was probably the fifth man I had met online in about a year who was couch surfing while he “looked for a place.”

There have been times when I’ve stopped dating while I worked various things out. I didn’t feel, for whatever reason, I was in a position to start dating anyone. I think it’s easier for a woman to do that, though, than it is for a man. Even in these times, women tend to expect men to be stable and secure. You are both. You’re not the problem. The problem for you is going to be how the women you meet perceive your situation.That’s why transparency is key.

Overall, I think people in some form of transition – out of work, in between apartments, bouncing back from an illness or injury – tend to be perceived as a liability in some way.  We wonder if their current situation will eventually pose a problem and make things more difficult. For me, I hated the idea of always being the one expected to host the sleep overs. It put unnecessary pressure on me. I can handle the out of work thing. I can deal with the financially strapped thing. But the couch surfing thing is something I don’t want to deal with. Am I being unfair or maybe a little too rigid? I’m sure. If I’m to be honest, someone sleeping on someone’s couch doesn’t exactly say, “Looking for a relationship” to me, either. That would be my main concern: what are they really looking for?

My concern for you, John, is that if you mention your job in your profile and then reveal your current situation in person, women will assume you were being deceptive. They’ll feel they were led on under false pretenses.  If you don’t mention your job and wait until the initial meeting to share that info, women might still feel deceived.

Sadly, I think a lot of people look for reasons to blow someone off.  Women especially. With all the paranoia out there about scammers and serial killers, some guys don’t stand a chance unless they provide a credit report and a blood test by the end of the first date. I was reading a website yesterday that offered classes on how women could verify academic/work history and determine a man’s approximate salary and rent payments. No joke. If they see a gap on your LinkedIn profile, you’re suspect. It’s ridiculous.  Here’s how you avoid being scammed: don’t give them any money and leave if they ask you for it. There. Simple. I think what women fear more than anything is feeling stupid for trusting someone who by all accounts presented themselves as too perfect. Here’s the mantra, folks: If it seems too good to be true, it probably is. Everybody lies. It’s just a fact of life. I know people who say that they’re “Ivy Educated” and it turns out they actually graduated from a  state school but went to a one year graduate program at an Ivy college. People do this stuff all the time. The problem isn’t really the embellishment. It’s our expectations and immature ideas about relationships.

That’s why I think John needs to make a brief mention of his situation in his profile. Something like:

“I’m anxious to get back to my job as a glass blower after a few months off due to an injury.”

Then he’s at least being upfront and won’t be selling himself in a way that will be perceived as dishonest. Undoubtedly, some women will take that and run with it and ask him what happened. That’s when he could offer more information.

Could it affect your prospects, John? Maybe a little. But those women who wouldn’t reply aren’t women you’d want to meet anyway. In which case, being upfront might be a good way to weed out the wrong people.

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14 Responses to “Do You Date While You’re In Transition?”

  1. Chris Says:

    Dead on with that response. I got laid off and I wasn’t sure if I should include that in my profile but I realized I didn’t want anyone to feel uncomfortable or have someone think I am scamming them. I try my best to give full disclosure so that the gentleman looking at my profile can make an “educated” decision on whether I am someone worth contacting. Moxie is right that women have less pressure on them to prove they are stable and secure financially. All my dates so far have thanked me for being honest in my profile, only one said even though he thought I was pretty my current situation bothers him and he feels like he would be paying my way…that was after he asked me about my current job and I told him, as stated in my profile, I am currently unemployed. I thought it was funny because it proved to me that some men just look at your pictures and don’t even bother looking at your bio. So John just be honest and like Moxie said “Could it affect your prospects, John? Maybe a little. But those women who wouldn’t reply aren’t women you’d want to meet anyway. In which case, being upfront might be a good way to weed out the wrong people” Good luck

    • Howard Says:

      Don’t let your situation hold you back. Most women will hold it against you, but there are women out there who aren’t locked into the materialistic mindset. The sad thing is that most men seem to be joining this material mindset also. We all place too much stock in the wrong things.

      If someone lacks material possessions because he or she is lazy, that is understandably a cause for concern, but that is not the case in your situation and most others.

      Past mistakes are tricky with which to deal. Everyone deserves another chance, but they should understand that there is a price to pay for past mistakes. However recovering from an accident should not hold you back from happiness.

  2. Amy Says:

    To the OP: I would present it like “I have a great job at XXX. I am almost done medical leave right now and will be back working again by YYY.” Then if wanted, he can say “The company has been great, the benefits have been amazing.” And THAT makes him (IMO) look MORE stable – to have a job like that in this day and age. Certainly the woman will likely want details, in which case I would keep them very brief and focus on the ‘almost fully recovered’ part. To be out of daily work for 2 years is a big part of your life story, and one that would probably come up in time. But not at the beginning.

    I know that for me, having gone through breast cancer, I have worked out a way, when it comes up, of handling it – not in dating, but in business situations, where people can be wary of working with someone they perceive as unstable as well. So if it comes up, I just say “Oh, that’s all done, I’m doing great now.” Big smile. And people seem relieved and happy to affirm that and move away from it. Nobody really wants to talk about medical stuff.

    If you stay upbeat and positive and future-oriented, I think it will be fine.
    GOOD LUCK! And congratulations on your recovery.
    PS @Mox – totally agree re the couch surfing. Early 20’s – fine. After that – Especially 6 mo. That’s not surfing. That’s lazing on a raft!

  3. Jack Says:

    Do you have any interests or passion projects that you can pursue? You can SO spin this in your favor. I would tell them that your company is working through some red tape and that in the mean time, you are working on a passion project (tell them about it). That kind of thing could really make you look good.


    • Andthatswhyyouresingle Says:

      No. No mention of “red tape.” Nor should he go the passion project route. He’s not 30. He’s 45. The days of pursuing passion projects are behind him. There is no spinning to be done here. The spinning is what will make him look deceptive.

      • Amy Says:

        I agree, but also think that he has to have SOMETHING to say about what he’s been doing (besides recuperating) for the last two years while not working. I hope it’s more than watching bad daytime TV.

        • Snowflake Says:

          WOW! Really? I know I am not a doctor but you do realise a neck injury is actually very serious. My gf was rear-ended a month ago. The guy slammed into her doing 65km/hr. She can barely move her neck, 4 weeks later still no improvement (she gets constant migranes can hardly sit at her computer longer than an hour, driving is painful, everything is painful) Neck injuries are not fun and the recouperating period is not a matter of months it does take years. Your abilities are restricted. This is exactly what Moxie just gave an example of in her dialogue above – how women will jump at anything to find fault/wrong with.

        • nathan Says:

          The days of passion projects are behind you? Are you kidding me! It’s very common for people in their 30s and 40s to realize that the work they are doing is not at all what they want to do for the rest of their lives. Some try and start new businesses. Others write books or pursue the artistic career they pushed aside to be “practical.” Still others go back to school to become something else. Hell, a lot of people keep the day job, while also developing these other interests on the side that one day might become the new day job.

          For the majority of people, the days of being locked into a single career for life are long gone. It sounds like John is fortunate to have a good work situation. However, if John has other interests he’s passionate about, I’d think he’d be more attractive than someone whose identity is mostly tied up with their job. Regardless, there’s no need to lie about the injury, or status at work.

  4. Snowflake Says:

    OP – John, I agree with Moxie. You should not hide anything, you have nothing to hide to begin with. What you have been through is completely normal and not out of this world. Great company, long standing relationship, the back to work start is just typical of what insurance companies can be like (regardless of healthy, auto or home). Be transparent, there is nothing wrong with doing so and as Moxie said, you will weed out the ones you should not be dating anyway. Good luck.

  5. offensivedan Says:

    I find myself agreeing with Moxie again which is stunning–to me, anyway. Yeah, people will find any excuse to blow you off. That’s especially true of women. Women always try to find what’s wrong with a guy and why they should not date him. It can be he’s not tall enough, he does not provide status and/or wealth or she is concerned what her family/friends will say. As I said in prevous post, this is why potential relationships get smothered in the cradle. WIth a women, unless you are Brad Pitt, you are starting from behind the eight ball.

    Anyway, moving on to the OP’s post. Personally, when I did not have a job, I did not not date. I just did not want to go through the awkward experience of telling some broad why I was unemployed.Women are so judgmental to begin with and, again, are looking for an excuse not to give you a shot. Most women will not be understanding of your situation OP. Sorry to say so. Also, when you tell them you were seriously injured in a wreck that will aslo work against you–even if you have recovered. Op, you see, most women, today, will not give you a legit shot to begin with and will just shut you down.

    Let me provide this real world example, too. Recently, I went out with this 42 year old woman. She was friendly but she was unemployed and had two kids. She did include in her profile that she had been laid off; rather, she waited to tell me when we talked on the phone. To be honest, at that point, I was suprised and did not want to meet her. But, she sounded like a sweet woman and she was attractive, so I did. Plus, she mentioned how she was cleaning houses to make ends meet, so that changed my mind, too.

    OP it’s up to you if you want to deal with this awkwardness. But, this is what you will run into and, most women, will not give you a shot or let you explain your situation. Why? Because they could care less and have other options–employed options that is. I would wait until the work issue is resolved.

    OP save yourself the hurt feelings and just wait till you are employed to date. Trust me on this. You don’t need your self-esteem to take a beating.

  6. offensivedan Says:

    Also, let me add this. Why do people insist on dating while in transition? It’s just not the unemployed but people who are separated and not yet divorced. I mean, when I don’t have my shit together the last thing I want to do is date. Why put yourself through this and add to the problems you already have?

    Being unemployed or separated are life altering events that are not easily dealt with or swept under the rug. To be honest, potential daters should be wary of dating an unemployed or separated individual. So, I amodifying my position in the previous post. Dating is hard enough but you don’t want to get attached to someone going through these issues.

    Again, my opinion is that the OP should not date. What’s a couple of more months till he gets back on his feet? It’s the same for separated people. WHy not wait a few months until the doivorce is final and you can move on? I dated a separated woman once. I will never do that again or date anyone in transition.

  7. DrivingMeNutes Says:

    I agree with Moxie’s advice here. However, I’d be more worried about being judged for my medical issues than for my lack of immediate employment. No one ever got rich betting on the compassion of others, particularly in the state of nature that is the dating world. Neck and back injuries or other “pain” disorders are immediately suspect because they can be faked and used for economic advantage. Also, if you had some role or fault in your own injuries, people will judge you for that too. If your injuries are healed and all in the past, they should not be disclosed for a while. You’re allowed to spin a tale in your profile. Just do as Moxie says and don’t raise red flags.

    As for giving up dating while unemployed, I think that’s both silly and impractical. Human relations and SEX are a driving force of life, just as is sustenance. Unless you are actually starving and survival is at issue, no one is realistically giving up sex until they find stable employment. Nor should they, in my opinion. Just need to adjust their expectations (downward, if that wasn’t clear)

  8. Andthatswhyyouresingle Says:


  9. Steve From the City Next Door Says:

    I was laid-off and went back to school to a top graduate school in my field of choice. Yet women still thought I was slacking or something. I would suggest skip it…at least anything serious.

    I had a date with a lady i was introduced to by a classmate. It was going great (or at least it seemed). I said something that and suddenly she realized I didn’t have a job…I wasn’t employer sponsored like her friend (i.e. that is he worked and they paid for his schooling). Suddenly things went sour. She did suggest that I contact her once I was back on feet. A few quarters later I ran into her at gathering held by that friend. She suggested we give it a go again..but it had to be “a real date” and I would pay. We did…it was fun but I learned somethings that made us clearly incompatible.

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