You really don't need to be anything special to find a woman, which is why billions of people around the world have found at least one in their lifetime, and billions upon billions more dating back hundreds of thousands of years. . . If he hit up the bars and hit on 50 short girls he might find one who's interested. He could probably approach that many women in just a couple of weeks if he was really dedicated to going out.
The month Kent tries to approach 50 different women he's interested in (1 or 2 a day on average) and is continually not letting the rejections he will receive poison his mentality on future approaches is the month he'll get about 15 real contact numbers and about five real dates from those collected digits in an average estimate. He's a long way from that now from what I can see, he approaches what,
a girl every other month? Add in the idea that Kent doesn't have enough quality repetitions doing this kind of thing and we can expect him to be a little less than average in successful courting scenarios so his first month of that level of commitment to the cause will probably bring in fewer than that 15/5 estimate of potential sweethearts from the ground up.
But ignoring that state of affairs, that's still 35 estimated flat out rejections Kent has to handle from the jump and 10 more chances to cry emotional tampon use down the line that will potentially kill his needed mentality to get to those five dates where romance might be in the air if everything goes good and he plays the right cards. Now you have to add in Kent's demands of no tats, no crazy jewelry, smells nice, etc. Again, that's going to lower his prospects and success ratio just from pickiness which is in effect raising the bar that you state is already so low just from his own perspective on what he's interested in. So bottom line is, Kent apparently needs a 100 to 200 times improvement of his courting behavior efforts to get to your example, and with that will come more rejection than he's used to that he'll have to be equipped to handle properly.
As I've said, I like Kentray, I'm cheering for him to improve himself and by extension his satisfaction with his relationships with the opposite sex, but he has a very long way to go just on that one front of this thing. On top of that, there is plenty of room for improvement in Kent's own life that he can work on to make himself feel better about his own self-worth that is even more important, IMHO, than the female companionship he's pining for. So while I don't disagree with your theoretical assessment here, I remain skeptical that at this time he's equipped to be able to do what you're describing at this moment, dedication to going out or not. Now after all that tl;dr, new Kentray Brown video time

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(Oh shit! Bassomatic is going to get to hear Kent's answer to OPL's playing house with lego shit female/kids voice in a future transcription! Already that gets another point on the Kent scale for this last video. 'Staying on my grind' is better than 'staying in my own lane.' Potential doesn't get anything by itself, it's only when potential is developed into a useful form that it can be employed for what it's intended. This is a lovequest video on par with some of the classic CWC videos, 'reproduce my seed,' almost ruined my laptop monitor. His new fade looked kind of fresh from the little he showed it off, the Cubs are in the series for the first time since the 40's and he just had to wear a south side getup, lol. Still, this entire video, and the last one too, is better as a list of wishes on paper that Kent then hides and never tells anyone that he has written down to compare to a potential committed relationship partner's attributes at a later date when he's considering getting more serious with a woman instead of a potentially female alienating public video on a very popular tube site that the world enjoys using every day, but then again, that's our Kent!)