The Dating Paradox

I have been single for the last 12 years.  It can get pretty lonely at times.  I’ve found it difficult to even land a single date with a woman, let alone find myself dating for several weeks in a row.  The one and only committed relationship I’ve been in was 12 years ago. It was the engagement that I have talked about several times.  We were only together for a year.  I had been single before that and I have been single since.  Sometimes I get loaded comments from people about my situation as if I haven’t been trying.  This is massively frustrating:  

  1. I’ve tried online line dating multiple times.  I’ve been on dates with a couple women but it takes a lot of sifting to get to any sort of connection online.  Let alone a full blown relationship.  I’m trying another round and I’m committed to staying the course.  I’ll admit that in the past I’ve looked at it as a quick fix.  I’ve realized that I’m expecting something really big to happen in just a couple weeks of being online. It’s just like anything else.  If I want a big result, I have to commit for the long haul.  Check it regularly and be patient.
  2. I’ve had friends try to set me up with people they know.  Sometimes I’m up for this and sometimes I’m not.  Sometimes people think a woman is a attractive and I don’t.  That’s the biggest challenge here.  It’s awkward without even having met the woman in question.  I’ve learned not to tip-toe around this.  If I’m not feeling it, I say so truthfully and directly.  If a friend stops trying to set me up because I never want to try, then they are welcome to that decision.  I don’t think I’m doing a woman any favors by going out with her when I know I’m not attracted to her.  I wouldn’t want that.
  3. More than anything, I have approached the situation directly.  If I meet a woman in a certain context and I find her attractive, I’m a straight shooter.  I approach.  This strategy has not been successful thus far.  I think I’ve been respectful.  I haven’t gotten angry or bitter from the rejection.  But it has not worked.  I’ve only met 1-2 women who have been receptive to it in my life.  The challenge is the fact that the older I get the harder I find it to meet women naturally.  I don’t do clubs or bars.  I don’t have friends who throw house parties regularly.  I’m not in college.  There are fewer natural overlaps.  So, I find myself going kamikaze, often.  There’s a women I see often in my neighborhood, or regular coffee shop, or at work, etc. and I think she’s attractive and I’d like to know more so I make myself known through small talk.  After a few of those interactions I ask.  No dice.  Yes.  It might make things awkward for a bit but I’ve done this so many times that I’m totally fine with ‘no’. She might be awkward which doesn’t make me happy, but, what do I do?  Nothing ventured.  Nothing gained.


When I do go out on dates things have tended to fizzle really quickly.  I’ve been in several situations (I’ve written about them before) where I went on several dates with a woman and things were going well and then suddenly, she breaks it off.  I’ve also asked many women on dates, with whom I thought there was some existing chemistry, only to get turned down and avoided, thereafter. Several years ago this was all leaving me really baffled, so I began asking my female friends about what I might be doing wrong.  All of them said that there was nothing wrong with my approach.  Also, they affirmed that I’m a good catch and I just have to keep trying (this has always been massively encouraging). I once got a chance to get feedback from a woman who I dated that suddenly cut things off.  It had been a few years since we had last talked.  I ran into her in my neighborhood.  We were still very friendly and I asked her, “What made you end it? It seemed like we were doing so well?”  Her response, “I really liked you, you’re in great shape, you’re handsome, you are super driven, and you know what you want out of life.  And it was a bit overwhelming for me.”  Wait, what?!  Now, this was, again, super affirming but really confusing.  A couple years prior to this a woman actually told me that I was too ‘perfect’. I thought she was blowing smoke at me to save my feelings from being hurt.  I figured she just wasn’t attracted and didn’t want to say it.  Maybe she was being honest. Who knows?  SMH…



I think it’s similar to what I said in the last post, when you grow people get intimidated by it.  The irony in all of this is the fact that I grew up terribly afraid of girls.  Just the thought of approaching a female would make me start to sweat bullets.  I was overweight and there were quite a few times when my female classmates were the perpetrators of the teasing that I experienced.  There were times when girls very openly expressed how unattractive and undesirable I was.  For many years after high school I had to work hard to detach those old stories of rejection from females, from the new stories of rejection from females.  I guess, to some extent, back then I could understand why I wasn’t liked.  I was overweight, introverted, and timid.  Now, it’s ‘I’m too attractive’, ‘I’m too ambitious’, ‘I’m too self disciplined’, and that’s all ‘too intense’.  And so on.  I laugh at it sometimes because it really is a ‘damned if you do, damned if you don’t’ situation.  Obviously, I’m not about to stop going BEASTMODE every single day of my life, just to make someone feel comfortable.  Also, I would argue that I’m a pretty personable guy.  I love learning about people’s stories and I remember obscure details about people and my interactions with them.  I legit love people.  So even if I am intimidating, I’m pretty positive I have the ability to make a woman feel comfortable and safe, if given the chance.  So where does this leave me?

Life has taught me that criticism will always be there in some way shape or form.  Both constructive and destructive.  I’ve been getting rejected by women since I was a kid and the reasons have run the spectrum.  If I’m going to get rejected anyway, I might as well get everything I want out of life.  I might as well not waste any of my time living inside the parameters of someone else’s reality.  I will always choose growth.  Based on what I’ve learned, that growth will make me even more intimidating for a lot of women.  God knows that’s not what I’m trying to do.  I would think that it would make me more attractive, but some people run into their own limitations.  I must have the faith to believe that there is a woman out there who will match my drive and celebrate my ambition.  In the meantime, I have to have the humility to know that I am not God’s gift to women.  I have to have the grace to not beat myself up when I get rejected and not become cynical with the whole process.  Finally, I have to have the endurance, courage, and confidence to keep trying.  Closed mouth don’t get fed…

The internet and technology have changed the way we relate.  I’ve learned that even a phone call is too direct sometimes.  I guess I got stuck in the past at some point.  I feel like there was a time in recent history where a man was considered chivalrous for being courageous enough to approach a woman directly.  I don’t know that it’s not the case, but I don’t know that it is the case, either.  I know that it’s the way I would prefer to do things.  That probably comes from knowing that I had such intense fear around approaching women when I was growing up and now I want to beat that fear into the ground.  I think I have been successful in that.  Now I’m open to try more indirect methods: text/email/networking through mutual friends.  Sometimes it’s unorthodox but the older you get and the longer you are single, the more you have to scrutinize your strict rules of engagement for validity.  No easy answers on this one.  If you’re single, I’m in the process just like you’re in the process.  I hope that’s comforting.

Remember, you can’t control when you meet that right person, but you can control who you are when you meet them.  And, the most important person you need love from, is you!

And, I love you!  God Bless!


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2 thoughts on “The Dating Paradox

  1. This is great Travis. Thank you for sharing with us!


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