The Compliment "Challenge"

Hi all,

I had an idea for a "challenge" (for lack of a better word) last winter when I noticed a fairly attractive Asian girl on campus, and the thought came into my mind again yesterday. I wanna run it by others in this forum to see if this is something I should actually try to pursue.

For context, I'm a 20 y.o. heterosexual male halfway through college who suffers from social anxiety, esp. when I have to talk/introduce myself to new people or I'm around a lot of people. I'm an introvert, so I'm shy and reserved at first, but funny and witty enough if you'd get to know me. Right now, I'm as single-since-birth as they come: never had a girlfriend, never have been intimate, never have been on a date nor asked out on a date. Also, I've never (to almost never) been complimented ("cute," "handsome") by females who aren't already platonic friends or family members (i.e. people I have no shot of dating). All the while, I've had plenty of crushes and confessed to a few of them since high school, but all to no avail. My self-perceived lack of dateability has sadly taken a huge toll on my confidence and self-esteem. I don't want anyone to go through this feeling, which is where my challenge comes in.

So here's my "challenge":

• Once I'm back on my college campus when classes start, I wanna try complementing women in my age group whom I don't know personally
• It would help if I myself and the specific woman are alone and not in a rush to get somewhere on time
• I would gauge how appropriate complementing is in each specific case
• I would probably say something along the lines of "Hey, I just wanna say that ______, and I hope you have a nice day." inserting a comment about her looks in general or a specific article of clothing she's wearing (being appropriate of course)
• If they don't wanna converse, which is fine by me, then I could exit and go about my business
• If they do happen to wanna converse, then I'll converse

My campus is small compared to other college campuses, but there are so many people that the chance of running into a random person twice in quick succession is fairly low. In theory, this seems like a good idea to me, but I'm not quite certain if it would turn out to be one. My intent is to get myself out of my comfort zone. Also, if I ever approach anyone to ask them out, or if I'm ever asked out, I can be more comfortable in the process. Let me know your thoughts and if this is something I should try. Thanks!

 

That's a great suggestion, thanks! Like I said before, this "challenge" is targeted at strangers, so complimenting on anything intangible can be difficult.

 

Thank you @Clarke and @phwrancesco for your feedback!