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DEAR DEIDRE: MY new boyfriend completely restored my faith in men. I felt totally confident around him and he made me feel so special.
Our sex life has been brilliant and I’ve been so adventurous mainly because I felt I could trust him – totally.
That was until my sister and I made a terrible realisation.
We’ve been together officially for three months and last month I was ready to show him off to my family.
Opening up my photos app on my phone, I invited my sister to check him out.
I was a little hurt when the only thing she could say was ‘Oh!”.
But then I saw how shocked she looked. Demanding an explanation, I snatched back my phone.
She wouldn’t answer, and said she needed a minute before dashing upstairs to the loo.
My stomach lurched as I imagined what was going on. Perhaps he had hurt someone, or was a drug dealer?
Eventually she came back down and admitted she’d slept with him a couple of years earlier.
I felt sick!
I’m 29 and she’s two years older than me. My boyfriend is the same age as me.
At the time she’d come home from a festival boasting about this incredible sexual encounter she’d had.
She went into plenty of detail about how he’d given her the most intense orgasm and now I can’t unknow.
The thing is he really likes sex outdoors and that was what she enjoyed also.
Even though it was a one off for her – I now feel incredibly uncomfortable about their history.
It’s so weird that he’s slept with us both. How on earth am I going to introduce him properly to the family – and my sister now?
I haven’t told him what I’ve discovered yet. The whole subject turns my stomach to be honest.
I’ve been avoiding him and he knows something’s wrong but how on earth do I tell him, ‘Oh yeah you slept with my sister?’
The rational part of my brain knows he hasn’t done anything wrong. He hasn’t cheated on me but still I feel so angry with him.
DEIDRE SAYS: You’ve had a big shock and it’s going to take time to come to terms with this knowledge.
It sounds as if you may have been betrayed in the past before but be careful not to let those experiences cloud your judgement here.
I read that you really like him, so when your mind goes down hurtful and unhelpful paths, remind yourself of the facts.
He has not cheated, this was in the past and we are all entitled to our own history.
He likes you and wants to be with you.
Don’t be tempted to find out any more detail about their encounter – the knowledge will only fuel insecurity.
Perhaps it’s worth talking to your sister and explaining how this knowledge has unsettled you. Ask your sister to keep the information private between you, her and your boyfriend.
No one else within your social group or family needs to know.
Your boyfriend is not the enemy here. When you are feeling ready, explain what you’ve discovered and ask for his reassurance. He is likely to feel uncomfortable about this discovery also.
It may help you to talk this through with a counsellor. My support pack How Counselling Can Help explains how to find a reputable therapist.
Dear Deidre’s Past Problems
From long-buried flings to risky dalliances, secrets from the past regularly surface in Deidre’s inbox.
One woman is haunted by a previous affair and lives in fear that it could destroy her current marriage if it ever comes out.
Another reader confesses to a fling with his best friend’s mother, worried that exposure would shatter friendships and family bonds.
And a third woman faces the terrifying possibility that a DNA test could reveal a secret affair, threatening to upend her family life and relationship.
HOW TO BUILD TRUST IN YOUR RELATIONSHIP
Trust is the foundation of any strong relationship, but it can take time, effort, and honesty to establish or rebuild.
- Open Communication
- Talk about worries, needs, and feelings honestly.
- Listen actively without judging or interrupting.
- Acknowledge each other’s perspectives.
2. Consistency
- Keep promises, even small ones.
- Be reliable in daily actions – this builds confidence over time.
- Show up when you say you will, emotionally and physically.
3. Accountability & Remorse
- Admit mistakes openly.
- Understand how actions affect your partner.
- Take genuine steps to make amends.
4. Quality Time & Presence
- Put devices aside and focus fully on each other.
- Regular check-ins help prevent misunderstandings.
- Shared experiences strengthen emotional connection.
5. Patience & Forgiveness
- Trust takes time to develop or repair.
- Forgiving past mistakes doesn’t mean forgetting, but it allows growth.
- Avoid rehashing old grievances constantly. Focus on building a positive pattern.
Trust grows when honesty, reliability, empathy, and patience become habits.
Both partners must be willing to invest equally, and the process can take weeks, months, or longer, especially after betrayal.
Ask me and my counsellors anything
Every problem get a personal and private reply from one of my trained counsellors within one working day.
Sally Land is the Dear Deidre Agony Aunt. She achieved a distinction in the Certificate in Humanistic Integrative Counselling, has specialised in relationships and parenting. She has over 20 years of writing and editing women’s issues and general features.
Passionate about helping people find a way through their challenges, Sally is also a trustee for the charity Family Lives. Her team helps up to 90 people every week.
Sally took over as The Sun’s Agony Aunt when Deidre Sanders retired from the The Dear Deidre column four years ago.
The Dear Deidre Team Of Therapists Also Includes:
Kate Taylor: a sex and dating writer who is also training to be a counsellor. Kate is an advisor for dating website OurTime and is the author of five self-help books.
Jane Allton: a stalwart of the Dear Deidre for over 20 years. Jane is a trained therapist, who specialises in family issues. She has completed the Basic Counselling Skills Level 1, 2, and 3. She also achieved the Counselling and Psychotherapy (CPCAB) Level 2 Certificate in Counselling Studies.
Catherine Thomas: with over two decades worth of experience Catherine has also trained as a therapist, with the same credentials as Jane. She specialises in consumer and relationship issues.
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