I have reconnected with a college friend (never dated) since a reunion 5 years ago. He is smart, funny, and successful. We have spent time with mutual friends over the years, since he comes to town for work every three months. He is very attentive to me, and my friends think he is still harboring a college crush. On our last get-together, he confided to me that he is not happy in his marriage – they have slept in separate bedrooms for three years and no longer have sex. Our other friends have mentioned many times that he is very unhappy in his marriage. He has twin children who will be leaving for college in about two years, and he said that he believes he will initiate a divorce if things don’t change.

What I haven’t told you is that I have had deep feelings for this guy for over three years, but I have kept my distance because he is married. Now that I have this information, I can’t stop thinking of him.

How can I keep him interested without crossing a line? I don’t want to be the “other woman”, and I will not make out with him or have sex with him (unless he is separated and has filed for divorce). I would have to be confident that his marriage is really beyond saving, because I don’t want to interfere. I am also not altering my dating life, since I know that there is no guarantee that things will work out for us – waiting around for 2 years seems foolish, and a little crazy.

What is your best advice for what can I do now to have the best chance with him later? I really like him, and I think we could be very happy together, when the time is right.


Ready for Lasting Love?
Ready for Lasting Love?
Ready for Lasting Love?
Ready for Lasting Love?

Dear Tami,

Let me start by ripping off the Band-Aid: you’re making a big mistake.

One of the core tenets of my coaching is that no man is “real” until he’s your boyfriend.

What that means is that, until you’re actually a committed couple — one that talks every day, sees each other 3-4 times a week, leaves weekends open for each other, makes plans in advance, talks about a future, and still gets along famously, you really don’t have anything except:

Hope. Fantasy. Projection. Potential.

No man is “real” until he’s your boyfriend.

Your college friend is all of these personified.

Let me count the ways that he’s not real — and certainly no one you should build your life around.

    • 1. He’s married.

2. He lives in another town, maybe another state.

3. You’ve never gone on a date with him in all the years you’ve known him.


4. He will not be available to go on a date for at least two years — and that is presuming that he does, in fact, separate from his wife, and immediately wants to start dating you — instead of taking a break from women or going on his local Tinder to see who’s out there.

5. Even if he does have these equal feelings for you, you will then be dating a separated (not divorced) man who lives somewhere else, thereby setting you up for a long-distance relationship. Not just an LDR, mind you, but one with a man who will be in no rush to get married, and would probably ask you to move to be with him (since he’s successful and likely rooted at his job.)

6. It’s not until THEN — a good 3+ years from now — that you’ll finally face the same long odds that every couple with an initial crush faces — will we actually be COMPATIBLE for 40 years? (Statistically speaking, the answer is no. Most crushes don’t result in marriage).

Keeping this barely flickering dream alive would be the WORST thing you could possibly do.

So, Tami, how does that sound? Not too good from this dating coach’s standpoint.

Which is why I apologize for not answering your original question about how to keep him interested in you for the next three years. Personally, I think keeping this barely flickering dream alive would be the WORST thing you could possibly do, and I wouldn’t want to enable such a choice. Sorry.

Try finding a local, unmarried man and you can actually be MARRIED in three years instead of first starting to date.