Jumping Jack Flash

A SUBWAY restaurant in Dawson, Texas.
Salvador Dali never had a Subway..

Jack wrote:


I really like your advice and outlook on relationships, and I never figured I’d be the one writing in, but here I am.  I am just getting out into the dating world after a 5 year relationship that started just after high school.  I dated quite a disaster of a girl and as a result, ended up skipping out on college, working a dead-end job, and going balls deep in debt.  Now, I am in the process of turning that around, but I’d like someone to join me on that journey, so I’ve been online dating.  However, it seems the women I am attracted to are either done with or finishing school, working professionals, or much more attractive than I am and they all either turn me down or go on one date and then call things off.  How do I increase my chances of finding someone I want to be with?  I don’t want to settle for anything less than what I want.  I did that once and was burned.



I like your ambition here.  I don’t settle either and I would never want to see anyone settle for less than what they want.  You are also in quite a predicament.  It seems as though you’re still in tee-ball and trying to date in the major leagues (yes, I know I don’t watch sports, but I know enough to make that analogy..you’re welcome).  In dating your last girlfriend, you became OK with being average and you’re now looking to turn that around, but you’re basically asking a woman to date a guy that could potentially be the typical loser or mooch.  My advice to you is to NOT date until you’ve turned things around.  Yeah, I know it can be lonely, but rejection can be too and it seems as though you’ve been rejected enough to seek out advice.  To me, one rejection is enough to “up your game”.  However, you will probably decide to bypass my advice and date anyway, so let’s run through a few things here:

You have a dead-end job.  How are you talking about that job online?  If you’re cooking fries at McD’s and your profile says “I am forming a solid career in the food service industry” but you’re revealing your fry cook career on dates, women will be disappointed, I can guarantee it.  If you are working at Subway but have dreams of being an artist, put down the 6″ roast beef, be an artist, and make a career.  Sandwich artist doesn’t count as real art.  The point I am trying to make is, you can BS all you want online, but when it comes down to reality, people will always see through BS and you’ll find yourself in a REAL predicament.  You need to get things started for your future.  Which leads me to my next point..

Education.  You say you’re picking people that are finishing or done with college.  Most women want someone on their intellectual level and when they find out you’ve skipped that route, chances are they’ll be let down.  I am not saying you need a doctorate to “hang with the ladies”, but any degree will help and it will also give you possibilities for the future.  Women want to see potential and see your potential to grow your future together.  Without a degree in today’s world, that won’t happen.

Debt.  This is tricky.  Debt is a pretty common thing these days and may be caused by your current job.  Once you’ve lined up a better career, hammered out a good personal foundation, you should see a decrease or elimination in your debt.  Make every effort you can to fix negative credit and get things rolling toward the positive.

One other thing you didn’t mention is that you may be choosing people that don’t “match” with your lifestyle.  For example, if you’re the grungy/smoker type, going for a wholesome looking non-smoker will almost certainly fail, as would be a grubby t-shirt and ripped jeans type going for a fashionable lawyer.  It’s not the clothes that matter, it’s the lifestyle.  People these days are looking for a commonality.  If the person you’re meeting can’t envision being comfy taking you to meet her friends or family, they’ll call things off before it ever gets to that.  If you feel they’re more attractive than you, change your appearance and take some pride in how you look (physically and fashionably).

If you’re doing laundry once a month and you can’t figure out how an iron works, you may want to invest some time into learning your way around a laundry room.  Also, think about purchasing a new wardrobe.  Swiss cheese boxers and ratty t-shirts with pit stains are fine if you’re working around the house, but not when you’re on a date.  Finally, for God’s sakes, don’t ever wear tennis shoes on a first date (unless you’re doing some sort of exercise).  Be yourself, but dress to impress in everything you do..you never know where you’ll meet someone special.