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Emailing asking someone out

My Advice

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Okay, I just started dating and asking for numbers again after several years of not having sex.


I was in a relationship with a wonderful woman for five years (bad timing or I'd still be with her) and then later when i was single fell for a woman who was bad for me (she put me in the friends zone, then flipped out when I gave up trying to get her, and then killed herself). Most recent girl I was interested in ain't happening right now -- maybe someday but not now-- so I am NCing her and focusing on other girls.


So I am going to just do the 'aloof' dating thing while going to grad school.


I just hit on this girl I have known a couple years who i am not 'too' close to.'

She always knew I was attracted to her and seemed somewhat interested but didn't wanna date at the time. I flirted like mad with her today, told her hot cute she was and how I am gonna persuade her to go out on a date with me, and she seemed to be eating it up and grinning like mad, but I didn't outright ask her out cuz there were too many mutual friends around.



But I emailed her afterward. I know it is better to ask her in person but there was no place to isolate and I like thinking out what I want to say. Will an e mail be a bad impression? I have just recovered from alot of crap so I am new to some of the smaller points of dating even if I get the general picture really well.





This is my e mail.



Title: you know I was serious.



----Wanted to bring this up in person but too many people around and it would make it ackward.

You know I was serious. (not about the marriage part haha).


I am very attracted to you. You're really cute (I LOVE your crooked smile, slavic looks, silky hair, and sexy accent) and your personality rocks. Your humor is alot like mine, you make me laugh when I am down, and you are mature for your age.


I actually hate giving compliments to girls cuz it is far less effective than games (which I am too tired for at this point) but regardless of your answer, your cool so it makes me feel good tweaking your ego.


I am not looking to jump into anything and have been 'just dating', but I am on my way to being financially secure and stable (I am working hard to get into lawschool and do well in this masters program), I don't cheat. I'm honest to a fault, and let's face it, I am very good looking and ummm brilliant.


You should let me take you out to dinner sometime. I gurantee I will make a better date than "rob or don or whatever their names are..."


I have been dating and getting alot of numbers lately but I can't pass up a positive opportunity when I see it.


Think about it.


We could have a fun time hanging out together.


Funny thing, I am very attracted to her. She makes me laugh and has a gorgeous russian accent, plus I love jewish girls for some reason. And yet I feel very aloof. For me, this question is to learn about dating since what I sent can't be undone anyway, and I feel good having sent it regardless.


Those who comment on the egotistical remarks, we have a rapport already so that wont bother her plus she tends to dig my cocky remarks.

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I would say that this is the kind of email that is the opposite of what you should write, but if you feel so confident of your repoire with her then who am I to judge?


I will say that the over-the-top compliments will fall on deaf ears for a vast majority of women who just think that you're either blowing smoke up their ass or else just desperate and saying anything to bed her. However, there are other women who might just eat this up. Who knows. Takes all kinds to make a world.


The way you lay out all your intentions is likely to come off as off-puting though, like you're either rushing things or trying to control the situation, a situation that hasn't even happened yet. Why present a resume? Why gush so much? Why not just call her up and say, "I thought you were cute. Want to go out sometime?"


A guy that is willing to just let his words speak for themselves, and doesn't have to make a big production, song and dance about it all is probably going to make you more interesting then the guy whose email is basically, "Look how freaking cool I am." You end just just coming accross like some kind of perverted peacock with it's feathers in a huff.

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It sounds like you are trying to sell yourself to her and there is no need to. If she likes you she likes you nothing you say in an email will change her mind, unless she did like you and finds this one awkward.


I would just say hey it was great running into you today. I know this great coffee shop around my way. Why don't we finish our convo there.

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Hmmm, makes sense. Good responses. Yeah. Should be shorter and just point blank. No compliments.


Drew, no, that was a joke between us. I don't want to get married and I explained in the e mail I don't want a jump into a relationship with anyone, just looking to take her out at this point.



Jettison, particularly good advice.

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That e-mail would be a turn off to me and come accross as creepy/cllingy. I would be fine with "It was great to see you today but with all those people around I didn't feel comfortable asking if you wanted to go out for dinner this Saturday night. If you're interested, and I hope you are, please send me your phone number so we can make specific plans for that night or for another night." Thanks."

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