i want to ask out my coworker but i feel like she is out of my league

[brianls]

Hey everyone,

 

So at my job we hired an assistant to help me with my work. she is BEAUTIFUL. totally out of my league. i'm an attractive guy i would say but she is able to pull men who are way more attractive then myself without trying.

 

Please excuse the whole "DO NOT DATE COWORKERS" thought and hear this out because I REALLY want to take this girl out.

 

She is 23 i'm 28 and she's super nerdy and we both share a lot of similar interests. we are also very similar that we are both home bodies and rather stay at home and play video games and chill. looking at her you would expect her to be a super materialistic air headed gorgeous girl that likes to go out to clubs and bars every weekend. But she is the total opposite.

 

She is a gamer/nerdy girl in a models body. she says she attracts a lot of men and that they all look at her in one way but dont realize she is totally not into the typical "pretty girl" pool. she said she has really bad social anxiety (which i have noticed.....but its really cute).

 

We go out to lunch daily and ive asked her if she was single and she said yes and that shes been single for a while. at work she doesnt have a phone in her office so she told me to give her my number on her phone. so i did, and noticed on her phone that she had like 50+ missed calls. she told me she doesnt like phone calls and it gives her anxiety. so i told her "ok i guess ill keep it to texts only" and then she was like "well you can call me :)"

 

so when i got back to my phone in my office after leaving her office, she sent a text saying "(her name) [your favorite assistant]". whenevr we talk she is super smiley and happy. a coworker of mine even told me "i think she likes you" because of her body language and the way she talks to me.

 

I dont want to overanalyze this more than i already have. But my doubts come into play because she knows i'm her SUPERIOR at work so she may be acting super nice for that reason. she's only helping me out for a month then shes leaving. so idk how soon to ask her out. there have been multiple opportunities during our conversations when i can throw in a "we should do that together sometime!" but i never do just to keep it professional.

[leogirl876]

Hey everyone,

 

So at my job we hired an assistant to help me with my work. she is BEAUTIFUL. totally out of my league. i'm an attractive guy i would say but she is able to pull men who are way more attractive then myself without trying.

 

Please excuse the whole "DO NOT DATE COWORKERS" thought and hear this out because I REALLY want to take this girl out.

 

She is 23 i'm 28 and she's super nerdy and we both share a lot of similar interests. we are also very similar that we are both home bodies and rather stay at home and play video games and chill. looking at her you would expect her to be a super materialistic air headed gorgeous girl that likes to go out to clubs and bars every weekend. But she is the total opposite.

 

She is a gamer/nerdy girl in a models body. she says she attracts a lot of men and that they all look at her in one way but dont realize she is totally not into the typical "pretty girl" pool. she said she has really bad social anxiety (which i have noticed.....but its really cute).

 

We go out to lunch daily and ive asked her if she was single and she said yes and that shes been single for a while. at work she doesnt have a phone in her office so she told me to give her my number on her phone. so i did, and noticed on her phone that she had like 50+ missed calls. she told me she doesnt like phone calls and it gives her anxiety. so i told her "ok i guess ill keep it to texts only" and then she was like "well you can call me :)"

 

so when i got back to my phone in my office after leaving her office, she sent a text saying "(her name) [your favorite assistant]". whenevr we talk she is super smiley and happy. a coworker of mine even told me "i think she likes you" because of her body language and the way she talks to me.

 

I dont want to overanalyze this more than i already have. But my doubts come into play because she knows i'm her SUPERIOR at work so she may be acting super nice for that reason. she's only helping me out for a month then shes leaving. so idk how soon to ask her out. there have been multiple opportunities during our conversations when i can throw in a "we should do that together sometime!" but i never do just to keep it professional.

 

You may want to find out that it's appropriate to date people at your place of work. Some companies have strict policies against that and if you're her superior, that could be weird.

 

If you are allowed to date, I'm afraid if you don't have the confidence to ask her out, she'll friend zone you and then it'll be awkward to work with her.

Edited July 22, 2016 by a LoveShack.org Moderator

[brianls]

You may want to find out that it's appropriate to date people at your place of work. Some companies have strict policies against that and if you're her superior, that could be weird.

 

If you are allowed to date, I'm afraid if you don't have the confidence to ask her out, she'll friend zone you and then it'll be awkward to work with her.

 

I totally agree with the thought of being friend zoned. she is working with me for another 2-3 weeks so I figured i would let it ride out until she leaves THEN ask her out. but then i feel like by then it maybe too late and she will probably friend zone me. But i don't want to do it too EARLY and seem EAGER. i'm trying to find a good balance because she is a girl that's used to getting all the attention in the world. I don't want to be just another one of those guys so soon you know? i just don't know when would be a good time. there's been moments when i could have asked her out but havent. for example we spoke about movies and how she's never seen the star wars movies. right there i was considering saying "we should watch it this weekend!" but i didnt. theres been other moments similar to that where i could have led it into asking her out but didnt.

Edited July 22, 2016 by a LoveShack.org Moderator

[todreaminblue]

hey brianis....i think if you want to ask her you have to have the guts to do it...it will take guts.....but if you really really like someone....not asking is a whole lot worse than possible rejection...doesnt matter how nervous you are when you ask....nerves are normal.....what really matters is that you simply ask.......deb

[brianls]

it's not that i'm necessarily nervous it's just that i dont know when is the right time to ask. ive only worked with her for a week.

[phineas]

it's not that i'm necessarily nervous it's just that i dont know when is the right time to ask. ive only worked with her for a week.

 

Dude.

A week?

Like a new guy going gaga over her has never happened before.

50 missed calls?

C'mon son.

 

Be different.

Rub one out every morning before work if you have to in order to keep your self control.

 

Look, she has been very forward with you and her rules of contact.

You can call her?

pshaww SHE can call YOU.

Cut back on texting also. let her come to you.

 

Yeah it isn't the manly man way but when it comes to the corporate environment i let the women ask me.

 

I never ask women.

Why?

too many teases looking to lead men on and cry stalker. 100% serious.

[frus69]

50 missed called doesn't mean anything. I have literally 120 unread messages, so what? they are sales messages

 

Ask her out wait till she leaves. It's only 2 weeks she won't friend zone you that quick

[scooby-philly]

Ok - I'm jk with the title.....not really

 

Listen - it's true. I've seen it. I was a nerdy self-conscious over-weight kid and young adult. I've put some weight back on but I'm still as confident as I was 2-3 years ago. So yes, women are attracted to men who CAN attract them. If you think you can, you will. Simple enough. Out of your league? You're older, more experienced (hopefully at least as wise) and probably make more money or at least hopefully take care of yourself.

 

Dude - I'm a firm believer - yes a guy needs to express interest early on to get the attraction, to get the spark, but there's a point where if you want a HEALTHY, BALANCED, MATURE, RELATIONSHIP........there's got to be some work on her end. Not in a mean or rude way - but a healthy partnership is about partners - so play the game a little and make sure she wants to play it with you.

[Emilia]

Yeah it isn't the manly man way but when it comes to the corporate environment i let the women ask me.

 

I never ask women.

Why?

too many teases looking to lead men on and cry stalker. 100% serious.

Agree. The corporate environment can be very tricky, extra caution is needed.

[Justanaverageguy]

So you only have a couple of weeks until she is leaving and not working for you. So the work part is not a problem - i think you can actually use it to your advantage. Seems like a pretty simple equation to me. Keep building the rapport. Try and make it just a little bit flirty like her messages back to you about being your favorite assistant.

 

If you are temporarily her "boss" you can play with that a little bit and make it a fun, flirty in joke. I haven't met this girl so I don't know what would fly and what wouldn't you can keep fairly low key and subtle or depending on how she reacts go for some slightly more obvious sexual innuendo regarding the boss and secretary relationship if you think that will play.

 

When she is leaving now you have established your little playful in joke about you being her boss you can use that as an excuse to ask her out for drinks. The boss does need to take her out for a drinks to say thankyou for all her hard work after all. Use the work situation to your advantage - there is no issue if you make your move in 2 weeks when she leaves. If she was going to be staying then the situation would be different.

Edited July 22, 2016 by Justanaverageguy

[elaine567]

 

If you are temporarily her "boss" you can play with that a little bit and make it a fun, flirty in joke. I haven't met this girl so I don't know what would fly and what wouldn't you can keep fairly low key and subtle or depending on how she reacts go for some slightly more obvious sexual innuendo regarding the boss and secretary relationship if you think that will play.

 

When she is leaving now you have established your little playful in joke about you being her boss you can use that as an excuse to ask her out for drinks. The boss does need to take her out for a drinks to say thankyou for all her hard work after all. Use the work situation to your advantage - there is no issue if you make your move in 2 weeks when she leaves. If she was going to be staying then the situation would be different.

 

Well that all depends if she is into that boss/secretary dynamic or not.

If she is not the same career path as he is, only younger and less experienced, then I guess she will not be very pleased at being treated as the "secretary" will she?

 

As others have said it is a tricky situation, he is her superior and as such it could get very messy, especially if she is not interested in him at all, bar being friendly co-workers and she starts to feel "threatened and harassed" at work.

Even without the legal implications, it will be terribly awkward if she says "Thanks but no thanks" and he still has to work closely with her.

I think as it is only a couple of weeks till she leaves, he should wait till then before he asks her out.

[brianls]

Dude.

A week?

Like a new guy going gaga over her has never happened before.

50 missed calls?

C'mon son.

 

Be different.

Rub one out every morning before work if you have to in order to keep your self control.

 

Look, she has been very forward with you and her rules of contact.

You can call her?

pshaww SHE can call YOU.

Cut back on texting also. let her come to you.

 

Yeah it isn't the manly man way but when it comes to the corporate environment i let the women ask me.

 

I never ask women.

Why?

too many teases looking to lead men on and cry stalker. 100% serious.

 

 

I just hope she's not one of those girls that has too much pride that she wont express any feelings or clues that shes attracted.

 

Ok - I'm jk with the title.....not really

 

Listen - it's true. I've seen it. I was a nerdy self-conscious over-weight kid and young adult. I've put some weight back on but I'm still as confident as I was 2-3 years ago. So yes, women are attracted to men who CAN attract them. If you think you can, you will. Simple enough. Out of your league? You're older, more experienced (hopefully at least as wise) and probably make more money or at least hopefully take care of yourself.

 

Dude - I'm a firm believer - yes a guy needs to express interest early on to get the attraction, to get the spark, but there's a point where if you want a HEALTHY, BALANCED, MATURE, RELATIONSHIP........there's got to be some work on her end. Not in a mean or rude way - but a healthy partnership is about partners - so play the game a little and make sure she wants to play it with you.

 

 

that is exactly it. her last bf was with her for 4 years and she said she walked in on him having sex with another girl. she said he started doing drugs and totally changed. she's been single for 1.5 years since.

 

as for myself. i'm far from fat, i go to the gym and she does to. i have my own place and a legit career/foundation. thats what i'm hoping she see's and i feel like she does cause this is a different field of work for her from her previous jobs (bars, restaurants, tanning salons).

 

I DO BELIEVE i can attract her. its just that i dont know how far i should go as to trying.

 

So you only have a couple of weeks until she is leaving and not working for you. So the work part is not a problem - i think you can actually use it to your advantage. Seems like a pretty simple equation to me. Keep building the rapport. Try and make it just a little bit flirty like her messages back to you about being your favorite assistant.

 

If you are temporarily her "boss" you can play with that a little bit and make it a fun, flirty in joke. I haven't met this girl so I don't know what would fly and what wouldn't you can keep fairly low key and subtle or depending on how she reacts go for some slightly more obvious sexual innuendo regarding the boss and secretary relationship if you think that will play.

 

When she is leaving now you have established your little playful in joke about you being her boss you can use that as an excuse to ask her out for drinks. The boss does need to take her out for a drinks to say thankyou for all her hard work after all. Use the work situation to your advantage - there is no issue if you make your move in 2 weeks when she leaves. If she was going to be staying then the situation would be different.

 

funny you say that cause shes very intrigued by the office gossip. for example i was talking to another coworker who has a 3 year old child and hes my age (28) and how she said he doesnt seem at all the type to have a kid right now. so she was interested as to how he met his wife, if the pregnancy was the reason why they got married. if the baby was an accident etc.

 

she also knows i stay at work very late (until 9pm some nights) and she asked if ive ever met the cleaning lady that comes in at night. she then went on and said she wonders if any of the higher up executives have hooked up with the cleaning lady. so the "kinky" mind is definitely there i would say.

 

 

other things i've picked up on her is whenever she says "ok" she would say "oTay" like a cute little thing. and she would only say otay around me when speaking. like when i tell her something to do she will be liek "otay :)" sounds stupid but i gobble that all up cause its cute as hell. other times we talk whenever she asks questions i will answer with a "mmmhmm" and she will be like "ok mmhmmm" and repeat it. even if i answered with an MMHMM to 3 of her questions in a row. she would repeat the mmhmm after me.

[brianls]

any other thoughts?

[preraph]

Of course she's acting nice because you're her boss. If you feel she's out of your league, she's out of your league. If she's tired of guys hitting on her, some of whom are probably in her league, why would she be anything but annoyed if you did, who know you are not in her attractiveness range?

 

By the way, people with anxiety disorders, any cuteness you're imagining gets old very quickly if they are so anxious they can't hold up their end of daily living.

 

If you ask her out, she'll feel obligated to go along with it or risk losing her job. If she goes along with it, then she'll feel you placed her in a no-win situation. You need to leave your assistant alone. She knows where you are and can always ask you out, but if she does, be sure to ask her "Is this a date" because it's not unusual to try to be social with your boss to solidify your position.

[biker23]

I feel her signs are strong enough to continue to push the rapport. Lunch everyday is already a lot. I just doubt it's purely a boss coworker thing given the short time she will be there. Unless she's trying to get hired full time? Don't know the details there.

 

Personally I would throw the out of my league out of the window. She's given enough signs.

 

I'd see if she wants to go for drinks after work. Casual, not a date. Hang out.

 

Be prepared it may turn into something else more quickly their her tenure at your workplace.

 

If it starts to move that way. Communication is always the best move. Don't assume anything. Talk about the work issue.

[phineas]

any other thoughts?

 

You mean someone that seems to think what you have in mind is a stellar idea?

Yeah wont be a lot of those people around here.

Use some common sense.

[brianls]

Hey all,

 

So she is getting really comfortable around me. her body language shows. she gets close to me when i'm directing her on what to do on the computer. she would practically be hovering me. she fixes her hair and "stretches" a lot when i'm around. she sways in her computer chair side to side when im around (maybe she's nervous?). When I threw away some papers in the trash can which is below the desk. i would literally only have an arms space worth to squeeze through from where she's sitting and i would graze her thigh. She didn't move out of the way or budge. I tested it with a 2nd piece of paper to throw out to see her reaction that time. once again she didn't move as if she wouldn't care if I had touched her thigh while doing so. SURE I CAN BE OVER THINKING BUT JUST SAYING.

 

So here is the friend-zone part. She randomly started talking about this one guy who started following her on social media who she has mutual friends with. she made him a cake (shes a cake maker on weekends) or planned on making him a cake but he refused to pay her. instead he said the only way she will get paid is if she hung out with him. She refused and thought that was creepy. she then told me he constantly spam texts her. huge paragraph long texts. she said he texts her and makes it literally seem like they are dating and shes his girlfriend. she's been ignoring him for a long time and now the guy has gone to the extent of reaching out to her mutual friends asking why she has been ignoring/avoiding him.

 

long story short I know once girls start talking about other guys that's the first sign of friend zone in the making right? or is it all NOT bad when other guys get brought up. In this case she clearly doesn't like the guy and just wanted to filter her thoughts about how creepy he is.

 

This is the first she's brought up a guy to my attention and i plan on smothering that little crack of "friend zone" EARLY. was planning on asking her out this friday to the movies. a couple of my friends are going to see Suicide Squad. a movie both she and I want to see. Is that a good idea? or should i make it just ME AND HER so she gets the point that its a DATE.

Edited August 2, 2016 by a LoveShack.org Moderator

[preraph]

Everything you described in the first paragraph is how comfy I am around my boss. I'm 63 and he's 40 and there's ZERO going on there. Comfort is not a show of interest. It's a show of doesn't care.

 

She's talking to you about her man problems and how skeevy she finds these guys who are trying to force her into going out with them.

 

But by all means, join the legion. Sounds like she can handle herself just fine.

[brianls]

Everything you described in the first paragraph is how comfy I am around my boss. I'm 63 and he's 40 and there's ZERO going on there. Comfort is not a show of interest. It's a show of doesn't care.

 

She's talking to you about her man problems and how skeevy she finds these guys who are trying to force her into going out with them.

 

But by all means, join the legion. Sounds like she can handle herself just fine.

 

Join the legion?

[brianls]

update:

 

she hungout in my office for the remaining half hour of her shift and I made a move physically. she was showing me her nail colors so i held her hand and felt the surface of her nails with my thumb. she also complained about her hair looking greasy and she undid her hair and i took the chance to feel it after she said "it feels so rough" so i felt her hair for a good minute. went to the extent of reaching back out a minute after to feel it more when she continued talking about it. when she left for the day she told me "ill text you when i land" because she is going to florida this weekend. is that a normal thing a friend or coworker would say? it was sorta random. not at all expecting that. maybe she slipped that out without thinking it through? i didnt receive a text as expected cause i never expect anything until it happens. but is that a good sign regardless that she said that?

[jdubinva]

update:

 

she hungout in my office for the remaining half hour of her shift and I made a move physically. she was showing me her nail colors so i held her hand and felt the surface of her nails with my thumb. she also complained about her hair looking greasy and she undid her hair and i took the chance to feel it after she said "it feels so rough" so i felt her hair for a good minute. went to the extent of reaching back out a minute after to feel it more when she continued talking about it. when she left for the day she told me "ill text you when i land" because she is going to florida this weekend. is that a normal thing a friend or coworker would say? it was sorta random. not at all expecting that. maybe she slipped that out without thinking it through? i didnt receive a text as expected cause i never expect anything until it happens. but is that a good sign regardless that she said that?

 

Missed the chance for some fun extra-curricular work my man.

[bachdude]

Look, you'll never know until you ask her out.

 

Just be confident, don't act like like you are drooling over her or acting too eager, but keep it flirty. Relax. Have a, "well if it works out that's cool. If not, that's cool too" attitude.

 

Then ask her out when her job is done there. Take her someplace fun (but keep in mind her social anxiety) where you two can laugh and just have a fun, light evening.

 

Stop worrying that she is out of your league. Confidence kicks you up several notches in the perceived good looks category.

 

Good luck, man!

[brianls]

that's exactly it. I have been playing it really cool but also leaving bread crumbs of "flirting" and I feel like shes biting.

 

But today I feel different. She posted this quote on facebook saying

 

"She's different now, he said. I was too much of an ******* to see how beautiful she really was. Her heart was beautiful, she cared so much about me, and I never understood why. I never treated her the way she deserves to be treated. Why I asked?" Because her love scared me. Her love was so intense. With her I really could have been happy. i almost forgot how beautiful her smile was. I forgot because she hasn't smiled lately. She just cried. It was a shame. She wasted so many tears for someone like me."

 

Her ex cheated on her. she walked in on him having sex with another girl. I believe they broke up over a year ago. One of the first times i took her out to lunch at work and we got on the topic of dating she spoke about it and how he recently reached out to her.

 

So now after seeing that post what should I feel? give up? I know this sounds so childish. But that quote clearly means shes not over him and is a scream to him to come back maybe?

 

what should I do? continue playing my role and just ignore this?

[elaine567]

that's exactly it. I have been playing it really cool but also leaving bread crumbs of "flirting" and I feel like shes biting.

 

But today I feel different. She posted this quote on facebook saying

 

"She's different now, he said. I was too much of an ******* to see how beautiful she really was. Her heart was beautiful, she cared so much about me, and I never understood why. I never treated her the way she deserves to be treated. Why I asked?" Because her love scared me. Her love was so intense. With her I really could have been happy. i almost forgot how beautiful her smile was. I forgot because she hasn't smiled lately. She just cried. It was a shame. She wasted so many tears for someone like me."

 

Her ex cheated on her. she walked in on him having sex with another girl. I believe they broke up over a year ago. One of the first times i took her out to lunch at work and we got on the topic of dating she spoke about it and how he recently reached out to her.

 

 

If he reached out to her recently and she is posting stuff like this you are going to get badly burned if you try and pursue this. She will probably use you to make him jealous.

Even if she isn't successful in getting him back, do you want to be with someone who is still pining for their ex?

I would start looking elsewhere if I were you.

[brianls]

But do you think its necessarily a bad sign that she posted that? Nothing good from that at all?