Shall I tell gel about my past? Agony aunt answers your questions

She insists I tell her about my murky past

Q: My girlfriend is demanding to know all about my past. She says we can’t continue as a couple unless I tell all about my previous relationships, jobs and brushes with the law.

A few weeks ago we were at a party when a very old friend of mine turned up and shrieked, “There he is, the old reprobate.” He was very drunk and started telling my girlfriend various “hilarious’”stories about our misspent youth. I literally had to drag her away.

Back home, I caught her going through my old bank statements and paperwork. She asked me about drug use, drinking and antisocial behaviour. I tried to make light of the fact, saying I was something of a scallywag back then, but she refused to let me off the hook.

She now says she needs to know everything about me and wants the names of former girlfriends, business associates, employers and mates. She’s made it very clear there are to be no more surprises. As I work for her father’s company she says she can’t risk scandal, humiliation or disgrace. If we’ve any chance of making it, then I am to spill the beans.

I’m deeply ashamed of many of the things I’ve done in my life, from blowing cash in casinos and ripping off mates to upsetting my parents – who no longer talk to me. I spent most of 2004 having sex for cash with women in order to pay rent. Don’t get me wrong, I had some absolutely brilliant times before I hit rock bottom (with the drink) and reinvented myself. But I can’t see my very proper girlfriend being too impressed to hear 

I used to be a player. 

Do I really have to tell her everything in order for our relationship to thrive?

Your girlfriend sounds a very bright woman. She’s already done some digging and has found out about your old debts and wild partying. I can’t imagine that it would take too much of an effort on her part to dig a little deeper and discover more. 

The reality is that it’s a small world and nasty secrets have a habit of coming out. She’s asked you to come clean with her. Can you really risk giving her the edited highlights of your misspent youth?

A: What if you and she now bump into another old friend, or even someone with a grudge against you, and he or she speaks up out of spite? You just don’t know how you are viewed or what others actually think about you.

The bottom line is you can’t play games. If your girl has asked for a fresh start you’ve got to give it her. She’s not going to like some of the more gory details, but it’s better that she hears everything from you, right now, so that she can inwardly digest and make a decision about a future with – or without – you.

I get the impression she rather likes you otherwise she would have walked away after the night of the party. Maybe she can see you’ve got spirit and a twinkle in your eye that she finds attractive.

However, I can’t imagine that when you explain about your parents no longer speaking to you that she won’t suggest a full apology (from you) and a reunion. 

That would certainly be my advice if you are to unburden yourself and start again.

Sex matters 

Q: My colleague and I have been having an affair for nine months and I thought it was heading somewhere. However, he’s just admitted he still has sex with his wife to keep the peace at home. I saw her recently and couldn’t believe how different to me she is. She is really dowdy – how he can fancy us both when we’re so unalike. Do I not mean anything to him?

A: Surely you must accept that your colleague is behaving very badly. He is cheating on his wife and misleading you. I suspect he’s thoroughly enjoying the best of both worlds while being grossly selfish and unfair. If his marriage is ongoing, and he’s still having sex with his wife, what is your role?

It doesn’t matter what his wife looks like. Stop wasting your time. Be proactive and find someone of your own. I don’t understand why you’re indulging this individual in the first place – and I don’t believe your bosses can approve.