It started when I was 21. After a year of dating someone, I was hospitalized for an ongoing medical condition, and decided to change my life by living like a reckless single.

I cheated on my girlfriend and broke up with her days later. I came to regret it as a major mistake, told her about it half a year later, and she forgave me.

Two years later, I met another woman, whom I’d told about my previous cheating, how I regretted it, and vowed that I’d changed.

We began a happy four- year relationship, during which I’d annually get extremely drunk with my single friends and go to a strip club. All hidden from my now ex-girlfriend.

I know it’s objectively considered cheating, and I feel extremely guilty, yet I kept doing it.

We split up a few months ago, without me ever telling her, which is even worse.

Since then I met an amazing woman. We had immediate chemistry and fell for each other.

I knew I had to change my life if I wanted to be her partner. I started taking better care of my medical condition, saw a psychiatrist for a mental illness I had for years, quit smoking, stopped drinking heavily and going back to strip clubs with my friends.

Before things get even more serious with this potential partner, how do I tell her about my past? The common saying is, "once a cheater always a cheater," but I want to show her that I've changed and wouldn’t hurt her in the same way.

But I also understand that someone's past acts in a relationship can be indicative of their future.

Former Cheater

There’s little time between “a few months ago” when you broke up and meeting this new woman.

Yet your tendency toward behaviour you later regret, has lasted for years.

Change the story you’ve chosen for yourself, as in “Yada yada, I was sick so…”

Grown-up, “amazing” women don’t accept excuses for repeated mistakes.

So, yes, tell her about your cheating, excess drinking, and strip club forays of the past (she’d eventually hear about them anyway).

But drop the “did it but regretted it” self-absorption and just say you’ve finally grown up and know better. Then prove it.

Warning: People who do a major makeover of their earlier weaknesses mainly to win over someone they desire, often revert if they’re ultimately rejected or the relationship ends.

Make your changes toward better physical and mental health, for you. That’s what’ll prove them real and lasting.

 

The guy I’ve been dating for two months recently learned he has to work in another country. He still wants to see me as much as possible before he moves there next month.

If I keep seeing him, I know my feelings will grow stronger and it’ll make saying goodbye harder. Should I end it now and not waste my time?

I’m open-minded about doing long distance. Should I raise it?

Uncertain

If he hasn’t suggested it, you’d be unwise to build greater closeness now before he leaves. You know your own emotional pattern and are already worrying about losing him.

Two months is still early dating. Keep regular contact and see whether that works or it trails off.

In time, you’ll both know whether to raise a long distance commitment… but remember, if you don’t get to have visits, at least every six months, it’s very hard to maintain a real relationship.

I’m a man, 42, divorced (fairly amicably) three years ago, with joint custody of two school-age children.

After four dates with a recently divorced woman, 34 (with no children), she’s expressed “love” for me.

It’s very flattering, she’s attractive, thoughtful, and good company, but I feel it’s too early and don’t know how to tell her without hurting her (her husband left her for someone else four months ago).

Too Much Too Soon

Be honest. Tell her it would be a disservice to both of you and your children to rush into a serious relationship.

It’s even too early to date exclusively so don’t let a set pattern develop.

Say that you can still go out together sometimes but she’s free to date others just as you are, since you’re both just getting to know each other.

Her reaction will tell you lots more about her – whether she’s desperately needy, or just happily feeling hopeful.