| Well, first of all, if you approach someone with the attitude of 'hey I'm ugly'--then he or she will sense that--which gets to the root of the real problem you have. I say forget about dating anyone right now. There are two things called: confidence and self-esteem. Without either of these two qualities you're fucked in a relationship (I speak from experience). I say take the money you would have spent on a date with this person and the effort you would have spent on a relationship with this person and focus on building your self-esteem. Maybe see a therapist or buy a book. Then spend the next six months building your confidence. Eventually you'll have no doubt about asking someone out and all your problems will be solved.
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AHmm, well how ugly is ugly? Ok, never mind that. No matter how splotchy your skin or how squishy your butt, there is someone out there equally frumpy for you. It's just a matter of finding your target audience and marketing yourself to appeal to what they are looking for, or at least what they don't mind looking at. Most likely that means starting online. Seeing as how you've already turned to strangers online for advice, turning to strangers online for dinner and heavy petting shouldn't be much of a stretch. Create a quirky, interesting and intriguing profile for yourself on one or two dating sites. List your accomplishments and hobbies, but whatever you do, don't sound desperate or say that you're "in search of a soul mate." That always freaks girls out. Start out by making a few pen pals, see if those develop into friendships, and then hope that once you meet in person, the relationship you've created in your imagination, er, your email account, isn't affected by your looks. But get a haircut and maybe a new outfit just for good measure. If nothing else, it will make you feel like you just came off of Queer Eye and are ready to take on the world.
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