The woman I’ve been dating for several months, whom I met online, is exciting in some ways, but disturbing in others. She has her own business, is smart, very attractive and sexy. She has a daughter, 5, whom I haven’t met.

She shares her home with her sister and her sister’s two children. They live outside my city, but she commutes to see me as she can do some business here.

I don’t know what to believe about her “story.” She’s told me fragments only – an ex who comes in and out of her life, her sister’s partner who’s been in jail for theft… there’s always something upsetting her.

We enjoy each other’s company, and the sex. Yet I even doubt if I know her real name. I’ve met no one who knows her.

But I know if I press for answers, it’ll be over.

Sex With A Stranger

There’s a reason children are warned about “stranger danger.” It’s because they haven’t the skills or experience to assess ahead what can come from the unknown.

You, by contrast, have the awareness to know when to be wary. You already have doubts. For whatever reason, some of her story doesn’t ring true to you.

For a casual relationship that has it’s obvious benefits of sex and periodic company, the vagueness may not matter that much.

Yet you’re “disturbed” by it. The reality is that you suspect parts of her life may eventually cause her serious problems. And you worry that these may affect you. (A jealous ex, for example?)

Better to confront her before you get more attached. Say it makes you uncomfortable to be told only snippets of drama.

There’s no real connection between you, despite the sex, when she can’t share more of herself.

If gentle questioning scares her away, then your instinct is likely accurate - there’s reason for you to doubt her, even to worry about being involved with her.

I’m a 75-years-young single expatriate living in Toronto for many years. But the winters are  getting to me and  I must escape them by travelling to warmer places.

I decided to try meeting a lady from Florida who’d consider living in Toronto for our summer (escaping Florida’s humid weather and hurricanes) and me living there for the winter.

So I got onto a singles site and responded to profiles which sounded suitable, to which I received half a dozen positive responses.

Now, how do I meet them all on a single visit there? One of them has invited me to her home.

Do I tell her the truth and see if she’s confident enough for me to meet those who could possibly be her competition?

Confused but Hopeful

It’s a new twist on seniors’ relationships and the phrase “fair-weather friends.” Plus a marketing opportunity for dating sites: “Trade your hurricanes and ice storms for sunshine and love.”

A promising idea. But your question raises the unpredictable factor of human emotion.

Will this woman accept being the contact point for your expanded search for The One?

Frankly, it’s crass to use her home as your base, even if your finances are limited.

Stay at an affordable hotel. Spend time with her alone for a few days and assess your compatibility. (And her credibility. See above question)

If she seems a good choice, discuss how the plan will work – who pays what, when, etc.

If not, make the rounds of your other respondents.

I hosted a birthday luncheon for my friend of 30 years, along with our husbands.

After lunch, at a bookstore, I found a collector’s item in my daughter’s field of study, put it down momentarily, and saw my “friend” buying it herself.

She hid the bag to her side!

I haven't contacted her since except to send her birthday wishes on the day. I’d already given her several gifts on a recent vacation together.

This woman’s beautiful, rich, and has a Master’s degree.
Years ago she was jealous of me, but I always blew it off. But her buying a book because I wanted it, feels so terrible to me. I don't want to be friends with her any longer.
I don't understand this behaviour when someone supposedly has everything. I guess they really don't, and are just lonesome souls.

Upset in California

Ellie – Your last sentence shows what you’ve known for years about her. Have compassion, but see her less.