Like Sex with Dr. Jess on FacebookFollow Sex with Dr. Jess on InstagramFollow Sex with Dr. Jess on TwitterSubscribe to Sex with Dr. Jess's channel on YouTubeSubscribe to Sex with Dr. Jess's RSS feed
Sex with Dr. Jess


September 27, 2021

Cheating Questions Answered

Cheating is more common than we’d like to admit, and the experience is shrouded in shame, which encourages those affected to manage their most difficult challenges and feelings in secret. This secrecy further reinforces feelings of shame, creating a burdensome loop that makes managing cheating a seemingly insurmountable task.

We need to break this cycle and talk about it, so this week, I invited your neighbours to share their questions about cheating so that we can open a dialogue and rebuild fulfilling, meaningful relationships.

Leslie from Midtown writes: How do I move on and trust someone again after my ex cheated?

Permit yourself to feel sad, mad, scared, insecure, unsure, embarrassed, excited, hopeful and the full range of emotions we experience after a breakup. Breakups involve a period of grieving, and the feelings of loss are not necessarily attenuated by the fact that your ex was imperfect (or worse). You can be relieved to be rid of them and still miss some of the feelings and experiences you shared. This doesn’t make you weak; it makes you human.


Use rational thought to remind yourself that your ex’s cheating was not your fault. You cannot affair-proof a relationship, and you are not responsible for anyone else’s behaviour.

Consider the perspective that trust is not something that is fully earned. It’s something that you decide to give, so work on building up your self-esteem so that you’re open to connecting and trusting others — friends, family members, and potential partners.

To boost self-esteem, I often ask clients to make a list of their best qualities and add to it weekly. They keep track of highs, accomplishments, new experiences, proud moments and compliments received. It may sound cheesy or self-absorbed, but if you want to build healthy relationships, you ought to know what you bring to the table.

Remember that there is no evidence that your ex’s behaviour will predict that of future partners. So if you’re ready to date again, focus on being present, getting to know your date(s), and tuning in to what you feel in their presence, rather than assessing whether or not they’re similar to your ex.

Sal from Yorkville writes: My wife, who cheated in the past, is travelling a lot for work, and I worry it could happen again. Do I talk to her about it?

Let her know how you’re feeling: worried, anxious, and fearful of losing her. Expressing your concerns is not the same as saying you don’t trust her.

You may be able to work through some of this on your own or with a therapist, but if you’re in a supportive relationship, you can express how you feel and ask for reassurance without making accusations. When you express your vulnerabilities and take responsibility for your emotions, a loving partner will be inclined to respond with care and support.

Carla from downtown writes: My boyfriend cheated on several of his exes and says he’d never do it again. How do I know if he will re-offend or if I can trust him?

Has he taken responsibility for cheating or does he blame outside sources? The latter is a red flag, as no one forced him to cheat.

You will never know for sure whether or not a partner will cheat, but if you build a foundation of understanding and trust, you may reduce (or at least better understand) the risk.

Talk about what monogamy means to you. What qualifies as cheating? Can you agree on a specific set of terms? Agreeing to sexual exclusivity amounts to inadequate shorthand. Instead, have a long-form discussion about what monogamy means.

Discuss your relationship values and what constitutes a fulfilling relationship, considering practical, emotional, sexual, social, and spiritual elements. Talk about your history with emotional expression and how you experience emotional connection and fulfillment.


Talk about your sexual values, including your desires, boundaries, concerns, insecurities, and fantasies. Discuss how you might deal with differentials in desire and the natural and unpredictable changes to your sex life that occur with time.

None of these are one-shot discussions. They require ongoing thought, expressions of vulnerability, and openness to considering multiple perspectives.

There is no litmus test to find out if someone will cheat, but if you talk about your relational, emotional, practical, and sexual expectations with specificity, you’re more likely to cultivate the understanding and compatibility required for a lasting relationship predicated on love and trust.

This piece was previously published by Post City.