“Do you think it’s a bad idea for me to get into that kind of commitment?”

Yes!

Yes.

You do not know enough about this man to make this kind of investment. Also, you’re trying to begin a romantic relationship with him, right? Why should that involve so much financial risk? The emotional stuff is enough.

He was using this other woman for her resources. Please don’t step into her place. You’re talking about “bringing in funds,” but you should not be paying for this connection.

Some perspective: you managed to meet two people during a very complicated year. Both men are not quite right for you in different ways. The first had potential, but he was too far away and you didn’t like the way he shared his company (or didn’t). This second person has so much figure out; he’s looking for a significant other/benefactor, and you’re in no position to help. The point is, there are many possible partners in the world. Clearly you’re capable of finding them.

What kind of partner do you need right now? Who would round out your life and how? Make a list of attributes, and I’m sure you’ll see why this latest man is not your person.

Also, think about what you need for yourself as a single person. Can you spend some of your energy on pursuing a path to income by way of a job you might enjoy? Something that gives you a solid foundation for life regardless of your partnership status? I just think it’s harder to make decisions when you’re floating in your own life.

Honestly, that’s the most important list to make right now. When you’re on your own, what do you want to do, see, experience, and get better at? When people can answer those questions about themselves, they wind up with better partners for the ride.

– Meredith

Readers, I’m sure we all agree that this business is risky. How can this letter writer find better opportunities for dating? What’s your advice based on the history here?