I Could Not Sleep with the Fat Woman

I wrote in to you a month or so ago about me (age 46, divorced for 6 months) maybe dating a large 200 pound woman that I met online who is really pretty but who I wasn’t sure I would be attracted to when it came time to fool around. You said to go for it and see what happens because otherwise you never know, and because I said she was a wonderful person. You asked me to report back with my findings.

Well turns out that fooling around with her was sort of like a science experiment that was only partially successful. We fooled around 3 times. First time I became soft after just around 10 minutes of activity. I told her this happened to me twice before in my life (years ago) and that I was not sure what was going on with me. I told her it could be because I hadn’t

slept with anyone since my wife and I split up – which could very well be true. However, I knew in my own head that she did the opposite of arousing me, unfortunately – but I did not say this to her. So this was a failed experiment.

Second time we fooled around, I first drank 3 drinks – and just yanked off her pants and gave it to her hard for a few minutes until I exploded. This was a successful experiment (for me) because I was able to complete the task. But it was not successful for her because I’m sure she thought I was a two-pump chump. We did not discuss the brevity of this encounter, fortunately.

The third time we messed around, it was like the first time – except that I went down on her. I discovered an odor – which made me want to gag right away. And this killed my firmness immediately. I told her at that time that “I have issues in my head regarding my ex”, and that I was sorry. So I did not mention to her anything about her hygiene. I told her that I needed time to get my head together and figure things out.

So I waited a week, and then I basically dumped her. I told her that I just didn’t think we are compatible – and that it is simply a gut feeling I have. I did not mention anything about her size, or the science experiments … but I did tell her that I really like her, and I hope we can be friends which is true.

The advice you gave me (to go for it and see) was good. Otherwise I just wouldn’t know about potential attractions to larger women, or about her specifically. So now I think I can move on and know more about myself and what I like or can like. What do you think?

Thanks for writing back and reporting your findings. I think you did a commendable job handling this situation because you tried multiple times (rather than rushing to judgment), and once you proved to yourself what the issue was – you then let her down easy, and preserved her feelings … you kept the karma good, and that is always an outstanding way to proceed. You were obviously very deliberate and kind with how you handled this – which makes you a very good guy in my opinion, Sir.

Take it from one midlife bachelor to another – being single again after having been married (or in a long-term relationship) is definitely difficult. You are in a period of rediscovery – and I think it is great that you have removed any potential prejudices or filters, and are trying different things/types to see what works for you at this age. Really that is the best approach for anyone. My advice is that you continue to cast a wide net, and experience the world for a while … and just see what you wind up really finding attractive. And if things don’t work out, just like in this case – keep the karma good, and create a respectful exit strategy. Treat others the way you wish to be treated – let that philosophy guide your actions moving forward.

Since you are fresh out of the gate with respect to dating at midlife, my suggestion is that you read the material found here on midlifebachelor.com in the Midlife Dating Advice section, specifically:

Fundamental Truths about Women and Midlife Dating Today
Midlife Bachelor Personal Makeover
Develop a Strategy for Midlife Bachelor Success
Reaching Midlife Bachelor Equilibrium

All of the above is good background material for someone freshly single at midlife, like yourself. All of my advice is, of course, simply my opinion – so I urge you to adapt the things you find on midlifebachelor.com to your own situation. Use what you can, adapt it as you see fit – and I also urge you to give back to this community by joining our Midlife Forum … where many others our age are either now going through something similar, or have gone though it in the recent past. We learn from one another – and you can hear the opinions of both men and women.

Good luck – please let us know how things go moving forward. Oh – I almost forgot to mention that your “science experiment” analogy above was exceptionally entertaining. Good work on that, too!