A
male
age
30-35,
anonymous
writes:I have had a crush on a girl I worked with for a year, but due to circumstances, I was unable to ask her on a date. I have thought about writing a letter flat out, but I think the mystery would be fun; although, I am a little worried that the letters would label me as a stalker. Let me know what you think.(also the letters will have a theme, and display my last initial stamped in wax at the bottom.)
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, anonymous, writes (2 December 2010): If you can wait till Valentine's day (Feb 14) that would be the time to card her an amusing card card, see what happens, and not seem creepy. You could pass it off as a bit of fun. A letter seems a bit desperate to me.
A
female
reader, aintnoangel  +, writes (2 December 2010):
 personally, i think it would be kind of exciting to have annon letters being sent to me; the air of mystery is always alluring. although, there is no guarantee that she will have the same feelings for you...
ultimately it is your choice; but really, in the end, what do you have to lose?
a tip, keep the letters casual. let her know that your interested in her, but don't put so much detail into it that it makes it creepy & stalker like...
best of luck in whatever approach you choose to take, xo
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A
female
reader, pixiegirls +, writes (2 December 2010):
 It may not be in your best interest to send a girl a letter (I assume you are asking her out) that appears anonymous. She may immediately see it as a stalking situation and not see the mystery letter as amusing. These days, people may feel more threatened than flattered receiving an anonymous letter. It could ruin your chances of being able to ever ask her out and could just creep her out.
Aside from the “stalking” idea she could get, she might not feel you are confident enough to talk to her and ask her out in person. She could see sending a letter as a cowardly or weak method of saying you like her enough to ask for a date.
If you still feel you would like to go the letter route, make is a short note, get to the point, and above all….sign your name and leave a cell number for her to reach you. If you are able to write a note to her, you could put something in it like “I wanted to be unique in approaching you …….”.
Good Luck!
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