General Dating Questions/workplace crush


Hi Larry,

I am in my early 30's and a little shy with asking girls out.  I work part time as an instructor at a graduate school.  I am attracted to a new instructor (who I also liked when she was a student).  She is 25 and broke up about three months ago from a relationship that lasted over a year.  Her reason was that she did not think it was developing into something long term.  Most of that time was spent long distance because she was in another state at a one year post graduate program.   

We have become friends, and often banter with each other.  We also go out together in small groups with other instructors.  I was going to ask her out, but one of my colleagues told me she "did not want to date or be involved with anyone right now."  I found out this 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-up.  I recently discovered that she actually did start dating this guy a few weeks ago.   

Since I was not supposed to know about them, I decided to ask her out anyway.  At first, I tried to be casual with asking her to dinner.  She did say yes, but due to our schedules, we decided to try another time.  I called her two more times after, but things kept coming up.  Finally, I tried last week and she said yes, but explained that she had "just started dating someone and wanted this to be a friendly dinner and did not want it to be awkward."

We went out this past Wednesday night, and had a nice conversation.  My question is about dealing with this and moving forward, since I will be seeing her weekly.  I thought about telling her how I feel, but am afraid things could get more awkward between us.  I thought about just asking her out once in a while just to show her I am still interested.  I was unsure what to do since she is not in a relationship with this guy yet.  At the same time, I do not want to continue pursuing someone not really interested in me.  

Thanks for your advice,

You sound like you've thought this through and are keeping an open mind, which is rare.  Once thing to understand off the top is that she IS in a relationship with this other guy.  They can call it "just a couple of dates", or whatever they want to, but when she told you that she had just started dating someone so your date needed to be a friendship deal, she was actually saying, "I have enough interest in this other guy that I'm willing to put all others aside and focus on where things can go with him".  That's a commitment however you want to call it.
If your interests are that great in her, and she's willing to continue to see you as a "friend", then by all means keep that occasional date night going.  I would do some typical high school BS once (only once)per date by saying something like, "Wow, you're such a great person.  It sucks that you're dating this other guy".  You just conveyed your interest and if the dinners continued after that, she's confirming her interest back.
What I wouldn't do, is drop the rest of your dating life or prospects until this is a real relationship between you two.  Early 30's is too late in the game to sit around and wait on someone.

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Larry Luv


There are no questions that I can not answer. I am well known for my no-nonsense, straight to the point answers. My answers may hurt your feelings, but they will be the truth. I always try to do my best to help one understand the WHY, not just the how or what.


I have been a relationship counselor in various aspects for over 15 years. I have counseled people from the lowest levels of the community to the highest. My training includes a number of certifications in behavioral science.

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I have numerous certificates in behavioral science, demeanors, and non-verbal communication. I also hold a Bachelors in FWP Psychology.

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