Dating in middle age, choosing a publisher, and making yourself heard

Dear Mr. Blue,

I am a corporate speechwriter and a copywriter. I am 55.5 and would like to meet the right man who enjoys words. I placed a personal ad but got a response from a man in Federal Prison. It seemed intrusive to ask how he landed himself there, so I didn’t respond. I’ve got many friends and I’m perfectly okay-looking. What should I be doing? Taking trips? Moving to another country with a shortage of middle-aged women? Making a systematic request to my entire list of acquaintances to ask them to produce one person? What would you do? I am about to give up.  

-Exhausted by Love

A runaway lover, text problems, and dinner duties

Dear Mr. Blue,

I’m a single 51-year-old who’s been enjoying the outdoorsy life in Denver for the past fifteen years. I have a nice condo, good friends, a great job in the tech industry. Up until a month ago I thought I had the ideal life—and then my lover of eight years left me for another woman. He said he’d met her through friends and that they’d “clicked” in some magical way he’d never felt before. After he told me, he still slept at my condo that night (albeit in the guest room), and then he was gone the next morning.

Exes, etiquette, and losing a spark

Dear Mr. Blue,

I can’t get over my ex. We dated a few years ago and when we broke up, even though it was mutual, I was devastated. At 22 years old, it was my first time being in love, and my first time being heartbroken. The relationship itself had been turbulent: he was a night owl and an alcoholic while I found solace in routine and generally healthy habits—except for the part where I would drop everything to be with him, at any time. Still, we found common ground in our worldviews, artistic sensibilities, and appreciation for the finer things in life, such as good food and luxurious hours spent in bed. He was very sweet and attentive when he wasn’t arguing with me about how long to stay at the bar. We started dating again about a year later, magnetically drawn to one another once again despite my better instincts, but I eventually dumped him over our conflicting lifestyles.