Question
I’m a man in early middle-age with not much experience with women. I’ve been fairly isolated for a long time and live a lonely life.
I go into a bookshop semi-regularly. There’s a woman who works there and I think she is very attractive, but didn’t think the feeling was mutual. She seems like a shy person too. I’ve never really said much to her, just the usual interactions between a server and customer. We’ve smiled politely at each other, but she has never given me any indication she liked me, until recently.
The second to last time I went in, as I approached the till to pay for my items, she greeted me with a big smile, more than just being polite to a customer. I wasn’t imagining it. No woman has ever smiled at me like that. Being the idiot I am, I panicked and didn’t say anything or meet her eyes again until she was handing me the bag with my books.
The look in her eyes was of disappointment, like: “What is wrong with you?” I just said thanks and left. I couldn’t stop thinking about it afterwards and realised that she wanted me to say something. So a month later I resolved to go back and ask her out. After an initial loss of nerve I finally asked her.
‘Although my current job has a structured career path and is secure, I find it meaningless’
‘I am divorced at 60, envious of my ex-husband’s new life and struggling with loneliness’
‘I’m dating a previously married man but I feel sad that I will always come second to his children’
‘A stranger entered our family and turned them all against us’
I was so nervous I could barely get the words out. I thought she looked nervous or even a bit frightened. As soon as I said it, she said, “Oh sorry, I have a boyfriend”, and bolted, couldn’t get away fast enough. I was crushed, then mortified and felt stupid for getting the wrong idea. I was raging at myself for upsetting her, especially in her workplace.
I haven’t been able to stop thinking about it though. Was that smile an invitation or nothing at all? It was the parting look that really got me though, like I had let her down. Is she angry at me for a perceived rejection? Has she written me off as a weirdo or timewaster who missed his chance?
I wasn’t rejecting her at all, I’m just terrible at speaking to women and people generally. When I was asking her the question, the room seemed to be moving. I thought I might faint. The last thing I want is to upset or frighten her any further. I am quite prepared to never go into that store or bother her ever again.
What should I do? I don’t even know her name or anything else about her. The only way I can contact her is to go back in to the store, but I worry she’ll freak out if she sees me again.
Answer
We know that the quality most highly rated among couples in a relationship is kindness and you seem to have that in spades – your concern for the object of your affections’ feelings and wellbeing show this. What this demonstrates is that you already have what is most desired in a relationship and what is needed is your own faith in your desirability.
The wonderful thing about desire is that whether we like it or not, it demands our attention and pushes us beyond our fears into taking a risk with another human being. In other words without risk and vulnerability there is very little possibility of a relationship – it is possible to have a one-night stand without taking this risk, but to progress to something deeper we have to take the risk of rejection.
You took the chance of asking this person out, and you did it on the basis of some sense that it might be well received, so well done you. It seems you have a sense of shame that you might have caused upset but we cannot take responsibility for other people’s reactions and indeed you cannot read her mind so you are guessing at what is behind her look as you left the shop. It was courageous of you to ask her out and you did it out of genuine admiration and hope, so do not retreat into yourself but instead applaud your braveness and let it be the start of something.
It is an honour to the other person to be considered worth you taking the risk of asking her out but she may be flustered by the attention and this is just fine. In order to address shame, we need to face it, so going back into the bookshop is a very good idea. Your intention here is to be yourself, smile and be kind, and speak to her if she is open to this – you will only know this in the moment. Your problem will be overthinking, so do this soon before your mind presents you will all sorts of negative possibilities.
You did, what for you and many people is, a courageous thing. You clearly would like to connect with someone so resolve to keep going and take any opportunity to chat with, or simply smile at, people you find attractive. Going further, perhaps now is the time to create an online profile, you might find a book on this in the bookshop, and again use the momentum that is now present to push you into the world of dating and possible romance.
Practising courage grows it, and you can trust that your innate kindness will direct you towards good future companions.
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