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I would greatly appreciate any thoughts on my predicament. I am a 53-year-old woman. I have a crush on a 26-year-old colleague (we have been colleagues for about half a year). He is always ready to help me and I was beginning to think that he liked me back. We seemed to have a special connection and I blatantly flirted with him.

It wasn’t until a night of partying when he got a bit drunk that he tried to touch my hand and held my hand as he walked me home that I realised he also liked me in a romantic way. After that night, we acted like nothing had happened, though I could see that he held back a bit, perhaps because he thought he had made a mistake.

I tried to make him feel comfortable by being my normal self, and trying to convey that what happened (his vulnerability that night) was no big deal. He can talk to other colleagues very easily, but seems shy around me and I always try to make him feel comfortable by initiating conversations. It's been a month since the incident and I think we are both beginning to be relaxed in each other's company and trying to return to our old selves.

I like him in a romantic way, but have no intention of pursuing a long-term relationship with him as I am much older than him and also my work contract ends in a year. It is obvious that I like him and he should know that. We both could sense that the crush is mutual and at times we could feel a little awkwardness between us.

My question is, should I tell him about my feelings and ask him whether he feels the same way and whether we can stay as good colleagues without the “romantic” element coming between us. I would like to make him feel better and more confident by telling him I like him back. I don't expect a relationship from this, but I do want to let him know that I like him back and perhaps maintain a friendship with him even after I left the workplace.

So should I even discuss what happened that night when he was a bit drunk? Or should we both carry on as if that night never happened, and disappear from each other's life when my work contract ends? He is a really great guy and I would like both of us to be great friends even after I left the workplace when my contract ends.

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    "should I tell him about my feelings and ask him whether he feels the same way" - if you do this, it may come across as if you want to begin a romantic relationship. However, you said in this message that you didn't want to pursue that. – Brandin Mar 2 '16 at 13:03
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    What do you want to achieve? By not talking to him you'll probably not get the relationship. By doing so, he may be alienated completely, or you might get the relationship. If you wanna remain great friends afterwards, just don't talk to him. My question is: what workplace issue is it that you're trying to navigate? – rath Mar 2 '16 at 13:12
  • Thanks for both your insights. I thought I should tell him directly that I feel the same way towards him to make him feel better and more confident, lest he thinks that I do not return his feelings. Perhaps when my contract ends I could tell him all these suppressed feelings? I just felt that life is too short - when you like someone, you should tell them, right? – S Sarah Mar 2 '16 at 13:25
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    You can remain friends after you leave. People can and do stay in touch after leaving an office. – Brandin Mar 2 '16 at 14:12
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    How would you have felt if, when you were 26 a 53-year-old male colleague had approached you about romantic feelings? Especially if you did not return the feelings. I think it would be much better to maintain a professional, relationship, no flirting, until you leave. After than you can tell him or not tell him with no pressure on him. – Patricia Shanahan Mar 2 '16 at 14:48
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It in doubt, wait, build a friendship, and let things go where they need to go, rather than trying to force a resolution. This is good advice for all relationships, moreso for office relationships. You're old enough to have learned this ... and to have learned that a crush is not love, and not always even serious interest.

Enjoy the feeling, but leave it there.

(BTW, if something does develop it's likely to be a lot more stable -- and to end politely if it ends -- if it started as a real friendship. I'm on good terms with everyone I've ever dated for just that reason. It's a lesson I wish more folks were taught before hurting themselves.)

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  • Thank you, Keshlam, for your insights and advice, and putting everything in perspective for me. – S Sarah Mar 2 '16 at 13:48
  • It may help that I'm in your age range and have had my share of "wouldn't it be nice if" reactions to younger colleagues... Thanks for putting up with my bluntness. – keshlam Mar 2 '16 at 13:55
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    Downvotes on the OP's prefered answer... sigh. I'm very aware this isn't Romantic advice. It's real-world advice. – keshlam Mar 2 '16 at 16:40
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I am a 53-year-old woman. I have a crush on a 26-year-old colleague...

Don't you remember what Aaliyah taught us?

It wasn’t until a night of partying when he got a bit drunk that he tried to touch my hand and held my hand as he walked me home...

That just barely passes the threshold for flirting. In another time, people would view this as "a gentleman helping a lady home".

I like him in a romantic way, but have no intention of pursuing a long-term relationship with him as I am much older than him and also my work contract ends in a year.

Unmarried people who like each other in a romantic way tend to act on those emotions. And since your work contract ends in a year, soon there will be no workplace conflict-of-interest.

In short, what you're experiencing is 100% normal. You should have explore these emotions with your colleague outside of the workplace. Good luck! I hope it works out!

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    It's so liberating to know that you feel the same way I do about age being just a number. Thanks for your insights. I neglected to mention that I this guy and I are from different cultures, and I am working in his country and will return to my home country when the contract ends. – S Sarah Mar 2 '16 at 13:44
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    Anyone who references Aaliyah here gets a +1 in my book. – Doyle Lewis Mar 2 '16 at 14:07

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