I'm in my 50s and have a crush on a coworker

Monday | August 19, 2024

Love Letters Dating

I’m in my 50s and have a crush on a coworker

I’ve never sought advice through a medium such as this. Please bear with me.

I’m in my early 50s. I’ve been attempting to get back into the dating scene after a long absence. To make a long story short, years ago I chose a career in radio over a relationship and possible marriage. Eventually I lost that job through a layoff, and my former girlfriend wound up marrying someone else. I lost the career and the relationship. The latter I’ve regretted for a long time.

At my current job I have a coworker I would love to get to know on a deeper level. I can honestly say that when I’ve talked to her, or she has smiled at me, I get a feeling that I haven’t gotten in a very long time – that “she could be the one” feeling, if you know what I mean. That said, for some time I’ve been wanting to ask her if she would like to get coffee, but my nerves and shyness take over. I go into a shell I can’t get out of.

This anxiety is so frustrating. If you could give me any type of guidance, I would be immensely appreciative. If I can somehow break through this anxiety and make this work somehow, I would be the happiest man on Earth. Thank you for your time.

– Anxious

Two bits of information that might help with the anxiety:

1. She’s not your soul mate. No such thing, really. What a relief, right?

2. She knows what it’s like to be shy and embarrassed – because most of us do. She is human, just like you, and will be OK, even if you ask her out in the most awkward way possible.

It sounds like your past relationship/work experience turned you into someone who is very concerned about the next step. You’re worried about regrets and making the wrong move, but isn’t it worse to make no moves at all?

This co-worker is a woman you like. That’s all. Assuming you’re not her manager in the office (that’s another letter), you could start by getting her some coffee. Instead of asking her to join you, you could say, “I’m grabbing a latte. Want anything?” That’s a very easy Step 1. (If people are standing around her, ask them too.)

From there, you can try again and see if she wants to join you.

If she doesn’t, it’s OK. There are so many other people out there. It’s not all or nothing with everyone.

I’ll also tell you to consider therapy to talk through whatever happened in that past relationship (and how it can mean less in the present). But the big note here is that your experience with this woman isn’t epic. It’s a work crush that could go away. Drop some of the reverence, and coffee might be more possible – and a better experience.

– Meredith

Readers? How does one reframe a work crush so it doesn’t mean everything?

What’s on your mind about your relationship life? Friendships? Dating? Divorce? Adjusting to change? Ask your own question. Use the anonymous form or email [email protected].

Dating Office Crush

Featured Comment

I think it’s wonderful that you feel ready to date again. Try not to allow past regrets to cloud current decisions- in this case, asking someone out on a date. It’s just a date, not a marriage proposal! Even if this particular woman isn’t interested, you’ll have had the courage to take a first step towards what you want in life. Good luck, LW.

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