It's a new week. Let's fix stuff.
Are you happy with your dating/partnered/single life right now? What do you need to know about what's next?
I am a 61-year-old woman. I have been divorced for 10 years and have not really had a relationship since. By all accounts, I look much younger than my age, especially with a mask on, which will be relevant in a moment.
I shop at a local gourmet cheese shop, and this very kind and adorable man who works there always remembers what I like and is always suggesting new things for me to try. Since we are both masked, I have no idea if there is flirting or if he is just friendly (and good at his job). I have a friend who knows him and says that he is in his mid-30s. So, here's my question. How inappropriate is it for a woman to flirt with someone, and maybe even show interest in someone that much younger? I fear that I look even younger with my mask on and that he would be horrified if he saw me without. I also fear that it has been so long since I've been interested in anyone that I am not reading signals correctly.
It is really difficult to find men my own age who have the same level of energy I have. All my friends think that I would have more success with a younger man. But THAT much younger? And is it unrealistic to think that a person that young would be interested in someone as old as I am? Thank you, and just sign me …
– Old and confused
The age thing isn't the problem for me. My red flag goes up because he's on the job.
He is friendly. He is good with cheese. And you know what? It's so wonderful to not be hit on while you're working! I mean, light flirting can be fine in life, and relationships – even the ones formed at a cheese shop – can evolve. But it sounds like he's not quite initiating the exchange of personal information. I would follow his lead when it comes to topics of discussion.
Now, if the friend who knows him says, "Oh, he has a crush on you," that's another story. Have you told this friend how you feel? Has she encouraged you? Does Cheese Man know the two of you share a mutual connection? It sounds you have a real source for intel. Maybe start there if the friend is someone you know well and trust.
Please know that my warning about misreading signals from someone who's working is not meant to stop you from thinking about romance. Cheese Man has reminded you that you can feel this way, and that crushes are excellent. My more practical advice is to try a dating app (a new one, if you've already done one). Give yourself a wide age range for prospects and court people who can see you without a mask. Practice flirting there. I mean, who knows, maybe Cheese Man is on the app, too. That would be quite a story if you matched there.
We get a lot of letters from people who say they don't feel their age – that they have energy, drive, excitement in their lives, the body (or top half of a face) of a 30-year-old, etc. That means there are other people who are a lot like you. Just remember to give them a chance too.
Readers? Have you worked in customer service? This kind of question has come up before, so if you have advice about how to read the room with someone who's working, that would be so helpful. Also, dating advice in general for this letter writer is appreciated.