She’s Almost Cheating With Me
In 2 years I will ask her to leave her boyfriend, but I don't want to wait around to see if she will.

Dear Rob,
Here’s the story:
I work with a woman, she is living with her boyfriend and has been with him for 4 years. She has one child from a prior marriage that lives with them. She has shown tremendous interest in me, and it almost got intimate, but we stopped before that happened.

We have always shared gifts at Christmas, etc. She knows I want her, but I have said the timing isn’t right because we can’t quit this job yet, until 2 years from now (big payout time). Then she could leave him financially and I could support her as well at that time.

She has never said she wants me, but has held my hand in the past, given me major signals as well. I asked her of she was single would she date me, she did say obviously.

In 2 years I will ask her to leave her boyfriend, but I don’t want to wait around to see if she will. Would you ask her point blank, are you ever going to leave your boyfriend? She may say she can’t predict the future. What would you do?

Hi Ned,
Honestly? What would I do?
I’d date someone else.

You’re putting your life on hold for a woman that really doesn’t feel much regret about almost carrying on an affair with someone, a woman that really can’t settle down, a woman that already has a record of sponging off men…
What do I think?

I’d head to the hills and not contact her anymore.

Look, if she can’t get her life together RIGHT NOW what do you really think will change in two years?
Two years while she’s sleeping with this boyfriend, knowing that she’s just using him and possibly waiting for you?

She really gives me the creeps.

Move on.
You deserve so much better.
Best wishes,