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General Dating Questions/asking girl out in workplace



Here is the situation.  I am 33 years old and not very good at the initial asking a girl out.  I work once a week as an instructor at a graduate school.  There are 12 of us instructors working together.  I am attracted to one of the new instructors (who I also liked when she was a student).  She is 25 and broke up over a month ago from a relationship that lasted over a year.  Her reason was that she did not think it was developing into something serious/long term.  

We have become fairly good friends, and often banter with each other.  On a side note, her birthday is at the end of this month.  

My question is if you have any advice, or if it is even a good idea, to ask her out.  I thought about a birthday dinner, but this may be slightly ambiguous as to the meaning.  Or perhaps just make things clear that I am interested in dating.  I think either way she answers may make things slightly awkward when teaching together, but I feel she is worth that risk.    

Thanks for taking the time to read this,

ANSWER: Hi Nick, thanks for your question.

The most important fact that sticks out in your question is that this girl is fresh off a break up.  This creates three specific issues, in my opinion, which I will explain below.  Please keep in mind these are just situations which I've seen happen before.

The first fact to consider is that this girl may not want to become involved with anybody right now.  She may enjoy being single, and enjoy taking the time to discover herself.  If this is the case, she will probably NOT be open to the idea of dating anyone right now.  

The second fact to consider is that she may be looking for someone to fill the void left by her ex.  Sometimes this is obvious based on the way she is acting towards you.  For example, if she is acting very close to you, explaining how bad her previous relationship was, etc, then she may be looking for that shoulder to cry on.  This doesn't mean she's interested in dating you.  This means she is looking for a man to provide comfort and support.  This is definitely a tricky situation, and it could lead to you getting hurt down the road.

The third situation is that maybe she did like you in the past, but I'm not sure about this because I don't know how close you two were when she was a student and you were an instructor.  

Personally, I don't think that asking her out for her birthday as a date is a good idea.  If there were more of you hanging out, then that would be fine.  However, at this point, I think it would be best if you all just hung out as a group for the time being.  I say this because I'm going out on a limb here, and giving you the safest answer based on your question.  If you want to write me back and give me more information, I could try and give you another reply, but based on what you told me here, I'd take this really slow.

Elle :)

---------- FOLLOW-UP ----------


Thanks for your advice.  I would say that the first situation sounds most accurate.  One of my colleagues told me that she said she did not want to be involved with anyone right now, unless there was a potential to become something serious.  

And if this makes a difference, even though she was in a relationship for over a year, she spent one year at a post graduate program in another state.  When we asked her about him (just before they broke up), she would say that "her love life is complicated."  It seems that with the long distance and not much progressing, she felt it was better to end the relationship.    

Me and her already hang out in small groups with our colleagues.  They have actually been pushing me to ask her out as well.  I guess that in the past, I have waited too long, and it didn't work out.  This was my original reason for asking to go out for her birthday.  I didn't want it to be a "date," but rather just spend time alone with her.  I also didn't know if it was a good idea to at least mention something so that she knows my intentions.    

Thanks again for your time  

ANSWER: Hi again Nick,

It's hard to say.  I mean, on one hand someone is telling you she said she doesn't want to be involved with anyone right now but says she would be open to it if there was the potential for something serious to come out of it.  I'm really not sure what her intentions are, and that statement kind of confuses me.  

Part of me wants to say that yes, this girl is sick and tired of men (or immature boys, depending on how you look at it) that are not committed to a serious relationship.  She wants a mature, long-term relationship.  Then, there's another part of me that is concerned over her timing.  I mean, to jump out of one relationship right into another seems a bit too much.  Then again, if she was unhappy in the relationship for a long time, the writing may have been on the wall.  That's a whole other ballgame.  I'll keep it simple for your sake.

How about you do spend some time alone with her, like meet up for a coffee or something.  If she's up to it, and to me, it sounds like she is, have a mature conversation about this subject.  Normally I do not suggest this, but it sounds like this has already been mentioned, so there's no reason why it can't be tabled again.  Ask her what she is looking for in a partner.  I wouldn't necessarily go right out there and tell her you are interested in dating her.  In my opinion, it's best to have mature discussions about what you want, experiences you had while dating, etc.  I know a lot of people disagree with me on this one, but I see no problem in discussing this with someone you know and feel comfortable with, and someone you will possibly date in the future.  On a blind date, yeah, that stuff is off limits, but in your situation, I do think you can both benefit from this type of discussion.

Let me know if that helps, or if you require anything further.

Elle :)

---------- FOLLOW-UP ----------


Thanks again for your advice.  I just wanted to give an update and see what you think.  I ended up asking if she wanted to go out for her birthday.  Unfortunately, I think she misinterpreted the question, because she thought I meant with the other instructors we work with.

Last Friday, I was going to be in her area after substituting and asked if she wanted to have dinner.  She did say yes, but was not going to get off from work until after 7pm.  Since I was off at 4pm, I did not feel like waiting, and we thought it was best to reschedule (perhaps this was a mistake on my part).

I found out when she told my colleague that she was "not ready to start dating or be involved with anyone at this time," it was because another guy (who also is an instructor, but in a different department) had started talking to her.  It may be a coincidence, but he began contacting her right about the time she broke off her prior relationship.

I have also just found out that she started dating this guy about two weeks ago.  This news was very confusing.  In my opinion, she seems very conservative with relationships.  He, however, comes across slightly as a "player."  Perhaps this is bias, but I don't see them being compatible.  

So my question is about your thoughts on proceeding from here.  It this a "rebound thing."  If so, should I continue forward to spend time alone with her, eventually letting her know about my intentions (since I am not supposed to know she is dating).  Should I just let this go and move on.

Thanks for reading,

Hi Nick,

I'm going to make this short - let it go.

There are millions of other girls on this planet.  To me, this one is not worth the time and effort.  She is either not ready to start dating/be involved or dating someone.  If he's a player, that's for her to decide, not you.  Don't waste your time wondering and waiting if these two will work out or not.  

So yes, let it go and move on.

Elle :)

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Hello! I would be more than happy to consider questions you may have concerning dating. I do believe I would be best answering questions from those age 25 and up. I cannot answer questions which require me to determine if someone likes you based on their actions. If you have questions regarding meeting the right person, interesting and fun things to do on a first date or any date for that matter. I can also answer questions regarding basic relationship problems you may be having, such as not meeting the right person, how to figure out exactly what it is you want in a partner, or issues you may be facing in your current relationship. I cannot answer questions that deal with physical or emotional abuse or other psychological issues. Please be advised that I cannot read the mind of another person, therefore I cannot answer a question which involves me trying to figure out what someone is thinking. I cannot answer a question which ask "Does he like me?", or "What is she thinking?". In addition, I will not answer questions with vulgar or slang language.


I'm in my early 30's, and have definitely experienced quite a bit. I've struggled with trying to find exactly what I'm looking for in a mate, and I've also been in situations where I settled for less than what I was looking for. I have enough experience to know that you need a very close friendship with a person, and need to have things in common. I've been in long term relationships, so I can definitely help out in that category. Probably the best thing I've ever done was to take a break from the dating scene to discover who I was, and what I was looking for!

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