A Man’s POV How it Makes Me Feel When… The Biggest Issues Faced While Dating

By WisdomIsmisery writer and founder of RealMenDontGossip.com.
Twitter @WisdomIsMisery.

A little background: I’m 29 years old. I have a decent moderately well-paying career. I have no kids. One day I plan to marry a beautiful woman. I’m not sure if I want kids, but I’m not against having kids. That is a decision I hope to make with aforementioned beautiful wife. With this in mind, below are five big issues I face when dating.

1. I don’t have a type. This is self-explanatory. I didn’t use to think I was picky until recently. A line-up of my ex-girlfriends looks like a red carpet waiting list for a United Nations party. I have less than any idea of what I’m looking for. I hope I’ll know it when I see it.

2. Where am I supposed to look for women? Where does a 29-year-old man meet women? I’ve asked myself this question a number of times. In college, you were always one plastic red cup filled with alcohol from meeting your next hook-up. I desire more than a hook-up now.

Honestly, meeting women isn’t particularly difficult. Maybe that’s an arrogant statement but it is what it is. For a man, meeting women is a numbers game. If you approach enough women, eventually one of them will give you their number. That’s the law of averages at work. Perhaps I should rephrase the question.

Where do I meet my wife? The club, bar, and dating sites seem arbitrary. Granted, I’ve stumbled on every serious relationship I’ve ever had so perhaps the no plan-plan is the plan? Maybe it is not the plan that needs adjusting; I’m just old enough to be conscious of the fact that I never had a plan in the first place.

3. Mo money, mo problems. I’m not rich and I likely never will be. Being rich is not a personal goal of mine. I like money and I like what money can do for you, but I don’t sit around obsessing over how to make money. I do obsess over accomplishing various goals, which might inadvertently lead to obtaining money. For example, I’ve spent the greater portion of the last decade paying off $30,000 in debt. I thought in the end I’d have a woman by my side to help celebrate this accomplishment, but more times than not, women opted – and I can’t blame them – to find the guy who was already financially established instead of working with the guy who would eventually be financially established. It seems now I’m destined to end up with the latter woman instead of the former. Whoever she is, I will always wonder if she would have stuck by my side during all those hard times I faced in my past living check to check and ramen noodle to ramen noodle. Further, will she stay there during hard times in the future? Is it this woman’s fault she wants an “established man” and I finally happen to be one?

4. Does everyone have kids? I don’t have anything against kids, and I’m not against dating someone who has kids, but does everyone have kids? I find it increasingly harder to meet people that do not have kids. This isn’t good or bad more than an observation. In terms of dating, this means from day one I know that if the relationship goes anywhere I’m agreeing to be a part of an instant family or as a woman with kids I dated told me, “You’re agreeing to date us, not just me. We’re a package deal.”

5. Every woman my age seems to want to get married, ASAP. This is a gift and a curse. My dating demographic is roughly +/- 5 years, which means, on average, I’m dating women 24 – 34. I don’t know anything about a “woman’s clock” but it seems to tick louder during this age range. I barely have enough time to get to know a woman before I’m hit with, “where is this going?” and she isn’t talking about the movies or dinner, she’s talking about nowhere or the alter. It can place a lot of undue pressure on every budding relationship I engage in.

Those are the top 5 issues I face dating as a single 29 year old man. What are some of yours?






  • http://twitter.com/Aleesha_Nash Aleesha Nash™

    Great POV!  It is horrible to have that “biological clock” pressuring anyone! Hopefully the right woman will approach you (this based off of your video blog).  If you find out the solution to #2… please post a blog on that too! I read a few years ago that Whole Foods was the place LOL — Maybe this is still true :) 

  • Jen

    Sigh. This sounds like my dating life (except # 5).

About Jennifer

Jennifer Kelton

I have created this blog and social dating community to turn negative dating experiences into positive ones. In fact, it’s the exact opposite of what the name implies. It was my own life’s multiple combo plate of bad date experiences that inspired me to create this supportive community. In the midst of my own search […]

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