Find a Dating Challenges Therapist
Whether you're navigating first dates, patterns in relationships, or building confidence in the dating world, working with a therapist can help you understand yourself better and approach dating with more clarity.
Dating can bring up a wide range of emotions—excitement, vulnerability, frustration, and sometimes confusion about what we really want. Many people find that past experiences, attachment patterns, or self-doubt show up in their dating lives in unexpected ways. A therapist who understands dating challenges can help you explore these patterns, build self-awareness, and develop healthier approaches to connection.
First Session makes it easy to find a therapist who fits your needs. Browse profiles, watch intro videos to get a sense of each therapist's style, and book a session when you're ready. Whether you prefer online or in-person sessions, you can connect with a therapist who can support you in building the confidence and insight you're looking for.
Ratiba Yasin
Registered Clinical Counsellor
Virtual Sessions in BC, NL, MB, AB, SK, and NT.
Waitlist
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Ratiba Yasin
Registered Clinical Counsellor
She/Her
Anxiety and Stress Management Skills, Depression, Familial and social relationships, Attachment, Boundaries and boundary setting, Aging, Break-up recovery, Burnout, Building Self-Care Routines, Career guidance, Confidence, Cultural Challenges, Dating challenges, Decision making, Effective communication, Emotional regulation, Family Conflict, Low Self-Esteem and Self Worth, Identity and Self-Exploration, Intergenerational trauma, Life transitions, Parenting, People pleasing, Understanding & Regulating Emotions, Stress
Anxiety and Stress Management Skills, Depression, Familial and social relationships, Attachment, Boundaries and boundary setting, Aging, Break-up recovery, Burnout, Building Self-Care Routines, Career guidance, Confidence, Cultural Challenges, Dating challenges, Decision making, Effective communication, Emotional regulation, Family Conflict, Low Self-Esteem and Self Worth, Identity and Self-Exploration, Intergenerational trauma, Life transitions, Parenting, People pleasing, Understanding & Regulating Emotions, Stress
Sabrina De Araujo
Registered Social Worker
Virtual Sessions in ON.
Waitlist
Sabrina De Araujo
Registered Social Worker
Anxiety, Anxiety and Stress Management Skills, ADHD, Assertiveness, Attachment trauma, Befriending the Nervous System, Blocks in Connecting with Self and Others, Burnout, Couples, Dating challenges, Effective communication, Depression coping skills, Identity and Self-Exploration, Interpersonal dynamics, General Mental Health, Maternal mental health, Nervous system regulation, Grief and Loss, Familial and social relationships, Understanding & Regulating Emotions, Self-esteem, Self-Criticism, People pleasing, Perfectionism, Mind-body connection, Depression
Anxiety, Anxiety and Stress Management Skills, ADHD, Assertiveness, Attachment trauma, Befriending the Nervous System, Blocks in Connecting with Self and Others, Burnout, Couples, Dating challenges, Effective communication, Depression coping skills, Identity and Self-Exploration, Interpersonal dynamics, General Mental Health, Maternal mental health, Nervous system regulation, Grief and Loss, Familial and social relationships, Understanding & Regulating Emotions, Self-esteem, Self-Criticism, People pleasing, Perfectionism, Mind-body connection, Depression
Nicole Lobo
Registered Psychotherapist
Virtual Sessions in ON, BC, SK, MB, NL, and YT.
Waitlist
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Nicole Lobo
Registered Psychotherapist
she/her
Parenting, Anxiety and Stress Management Skills, Burnout, Attachment, Assertiveness, Borderline Personality Disorder, Boundaries and boundary setting, Building Self-Care Routines, Break-up recovery, Confidence, Couples Therapy, Dating challenges, Emotional regulation, Familial and social relationships, Family issues, Family Conflict, Women's Health, Workplace stress, Understanding & Regulating Emotions, Supervising qualifying therapists, Stress, Social anxiety, Self-Development, Relationships, Pregnancy, Postnatal Care
Parenting, Anxiety and Stress Management Skills, Burnout, Attachment, Assertiveness, Borderline Personality Disorder, Boundaries and boundary setting, Building Self-Care Routines, Break-up recovery, Confidence, Couples Therapy, Dating challenges, Emotional regulation, Familial and social relationships, Family issues, Family Conflict, Women's Health, Workplace stress, Understanding & Regulating Emotions, Supervising qualifying therapists, Stress, Social anxiety, Self-Development, Relationships, Pregnancy, Postnatal Care
Divya Gulati
Registered Psychotherapist
Virtual Sessions in ON, BC, MB, SK, NL, YT, and NU.
Waitlist
Divya Gulati
Registered Psychotherapist
She/her
Low Self-Esteem and Self Worth, Relationships, Childhood trauma, Anxiety, Depression, Anxiety and Stress Management Skills, Boundaries and boundary setting, Burnout, Emotional regulation, Life transitions, Attachment, Familial and social relationships, Trauma, Break-up recovery, Building Self-Care Routines, People pleasing, Meaning and purpose, Empowerment, Self-Development, Dating challenges, Blocks in Connecting with Self and Others, Intergenerational trauma, Self-esteem
Low Self-Esteem and Self Worth, Relationships, Childhood trauma, Anxiety, Depression, Anxiety and Stress Management Skills, Boundaries and boundary setting, Burnout, Emotional regulation, Life transitions, Attachment, Familial and social relationships, Trauma, Break-up recovery, Building Self-Care Routines, People pleasing, Meaning and purpose, Empowerment, Self-Development, Dating challenges, Blocks in Connecting with Self and Others, Intergenerational trauma, Self-esteem
Ashley Wass
Registered Psychotherapist (Qualifying)
Virtual Sessions in ON.
Waitlist
Ashley Wass
Registered Psychotherapist (Qualifying)
She/Her
Boundaries and boundary setting, Relationships, Understanding & Regulating Emotions, Anxiety, Burnout, Emotional regulation, Stress, Break-up recovery, Dating challenges, People pleasing, Women's Health, Relationship anxiety, Deep connections, Grief and Loss
Boundaries and boundary setting, Relationships, Understanding & Regulating Emotions, Anxiety, Burnout, Emotional regulation, Stress, Break-up recovery, Dating challenges, People pleasing, Women's Health, Relationship anxiety, Deep connections, Grief and Loss
Lindsay Kudlow
Registered Psychotherapist
Virtual Sessions in ON.
Waitlist
Lindsay Kudlow
Registered Psychotherapist
she/her
ADHD, Anxiety and Stress Management Skills, Assertiveness, Attachment, Boundaries and boundary setting, Break-up recovery, Building Meaningful Connections, Childhood trauma, Confidence, Complex Trauma (CPTSD), Conflict resolution, Effective communication, LGBTQ2IA+, People pleasing, Low Self-Esteem and Self Worth, Empowerment, Familial and social relationships, Relationship anxiety, Dating challenges, Navigating challenging relationships, Relationships, Trauma, Understanding & Regulating Emotions, Anxiety, Self-esteem
ADHD, Anxiety and Stress Management Skills, Assertiveness, Attachment, Boundaries and boundary setting, Break-up recovery, Building Meaningful Connections, Childhood trauma, Confidence, Complex Trauma (CPTSD), Conflict resolution, Effective communication, LGBTQ2IA+, People pleasing, Low Self-Esteem and Self Worth, Empowerment, Familial and social relationships, Relationship anxiety, Dating challenges, Navigating challenging relationships, Relationships, Trauma, Understanding & Regulating Emotions, Anxiety, Self-esteem
Kaitlin Klimosko
Registered Clinical Counsellor
Virtual Sessions in BC, AB, SK, MB, and YT.
Waitlist
Kaitlin Klimosko
Registered Clinical Counsellor
she/her
Anger Management, ADHD, Attachment, Anxiety, Building Meaningful Connections, Childhood trauma, Conflict resolution, Depression, Trauma, Court Mandated Counselling, Eating disorders, Stress, Burnout, Assertiveness, Dating challenges, Effective communication, Emotional regulation, Men's issues, Parenting, Self-Regulation
Anger Management, ADHD, Attachment, Anxiety, Building Meaningful Connections, Childhood trauma, Conflict resolution, Depression, Trauma, Court Mandated Counselling, Eating disorders, Stress, Burnout, Assertiveness, Dating challenges, Effective communication, Emotional regulation, Men's issues, Parenting, Self-Regulation
Katie Harry
Registered Provisional Psychologist
Virtual Sessions in AB.
Waitlist
Katie Harry
Registered Provisional Psychologist
she/her
Anxiety, Stress, Grief and Loss, Anxiety and Stress Management Skills, Attention and Impulsivity, Blocks in Connecting with Self and Others, Boundaries and boundary setting, Break-up recovery, Building Self-Care Routines, Burnout, Childhood trauma, Conflict resolution, Dating challenges, Depression, Emotional regulation, Life transitions, Parental divorce, PTSD, Self harm, Suicidal ideation, Workplace stress, Family Conflict, Identity and Self-Exploration
Anxiety, Stress, Grief and Loss, Anxiety and Stress Management Skills, Attention and Impulsivity, Blocks in Connecting with Self and Others, Boundaries and boundary setting, Break-up recovery, Building Self-Care Routines, Burnout, Childhood trauma, Conflict resolution, Dating challenges, Depression, Emotional regulation, Life transitions, Parental divorce, PTSD, Self harm, Suicidal ideation, Workplace stress, Family Conflict, Identity and Self-Exploration
Emma Cheuk
Registered Social Worker
Virtual Sessions in ON.
Waitlist
Emma Cheuk
Registered Social Worker
she/her
Attachment trauma, Depression coping skills, Anxiety, Attachment, Familial and social relationships, Dating challenges, Low Self-Esteem and Self Worth
Attachment trauma, Depression coping skills, Anxiety, Attachment, Familial and social relationships, Dating challenges, Low Self-Esteem and Self Worth
Lea Konforte
Registered Psychotherapist (Qualifying)
Virtual Sessions in MB, YT, NU, AB, NT, NL, BC, and ON.
Waitlist
Lea Konforte
Registered Psychotherapist (Qualifying)
She/Her
Anxiety, Relationships, Infertility, Fertility, Life transitions, Attachment trauma, Autism Spectrum Disorder (ASD), Break-up recovery, Burnout, Chronic and acute illness, Conflict resolution, Dating challenges, Emotional regulation, Family issues, Goal Setting, Intergenerational trauma, Mind-body connection, Nervous system regulation, Negative thinking and ruminating, Spirituality, Stress, Workplace stress, Grief and Loss
Anxiety, Relationships, Infertility, Fertility, Life transitions, Attachment trauma, Autism Spectrum Disorder (ASD), Break-up recovery, Burnout, Chronic and acute illness, Conflict resolution, Dating challenges, Emotional regulation, Family issues, Goal Setting, Intergenerational trauma, Mind-body connection, Nervous system regulation, Negative thinking and ruminating, Spirituality, Stress, Workplace stress, Grief and Loss
Melissa Milligan
Canadian Certified Counsellor
Virtual Sessions in MB, AB, BC, and SK.
Waitlist
Melissa Milligan
Canadian Certified Counsellor
She/Her
Anger, Attachment, Building Meaningful Connections, Abuse (Sexual/Physical/Verbal), Anxiety and Stress Management Skills, Behaviour, Burnout, Deep connections, Childhood trauma, Chronic Illness, Dating challenges, Boundaries and boundary setting, Depression, Intergenerational trauma, Low Self-Esteem and Self Worth, Navigating challenging relationships, Sexuality, Self-Development, Mindfulness
Anger, Attachment, Building Meaningful Connections, Abuse (Sexual/Physical/Verbal), Anxiety and Stress Management Skills, Behaviour, Burnout, Deep connections, Childhood trauma, Chronic Illness, Dating challenges, Boundaries and boundary setting, Depression, Intergenerational trauma, Low Self-Esteem and Self Worth, Navigating challenging relationships, Sexuality, Self-Development, Mindfulness
Michael Chu
Registered Psychotherapist (Qualifying)
Virtual Sessions in ON.
Waitlist
Michael Chu
Registered Psychotherapist (Qualifying)
He/Him/His
Aging, Anxiety, Boundaries and boundary setting, Burnout, Childhood trauma, Competitive anxiety, Conflict resolution, Cultural Challenges, Dating challenges, Decision making, Deep connections, Depression, Dreams, Effective communication, Emotional regulation, Empowerment, Existential questions, Ethics, Familial and social relationships, Grief Processing, Imposter syndrome, Interpersonal dynamics, Intergenerational trauma, Low Self-Esteem and Self Worth, Meaning and purpose, Motivation, Negative thinking and ruminating, Social anxiety, Stress, Thought Restructuring, Transformative dream work, Transitioning into Adulthood, Trauma processing, Understanding & Regulating Emotions, Vulnerability, Wellness Counselling, Workplace stress, Trauma, BIPOC, Grief and Loss, Identity and Self-Exploration
Aging, Anxiety, Boundaries and boundary setting, Burnout, Childhood trauma, Competitive anxiety, Conflict resolution, Cultural Challenges, Dating challenges, Decision making, Deep connections, Depression, Dreams, Effective communication, Emotional regulation, Empowerment, Existential questions, Ethics, Familial and social relationships, Grief Processing, Imposter syndrome, Interpersonal dynamics, Intergenerational trauma, Low Self-Esteem and Self Worth, Meaning and purpose, Motivation, Negative thinking and ruminating, Social anxiety, Stress, Thought Restructuring, Transformative dream work, Transitioning into Adulthood, Trauma processing, Understanding & Regulating Emotions, Vulnerability, Wellness Counselling, Workplace stress, Trauma, BIPOC, Grief and Loss, Identity and Self-Exploration
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Therapy is hard work.
Finding the right therapist shouldn’t be. Over 10,000 Canadians found their new therapist with First Session.
How can therapy help with dating challenges?
Therapy can help you understand patterns that may be affecting your dating life—whether that's anxiety around rejection, difficulty setting boundaries, or repeating unhelpful relationship dynamics. A therapist provides a safe space to explore your experiences, build self-awareness, and develop practical skills for healthier connections.
What should I look for in a therapist for dating issues?
Look for someone you feel comfortable opening up to. It can help to find a therapist with experience in relationships, attachment, or self-esteem. On First Session, you can watch intro videos to get a sense of each therapist's personality and approach before booking.
Is therapy for dating challenges only for people who are single?
Not at all. People in various stages of dating—whether single, casually dating, or in the early stages of a relationship—may find therapy helpful. It's about understanding yourself better and improving how you relate to others, regardless of your current relationship status.
How do I know if I need therapy for dating challenges?
If dating consistently brings up difficult emotions, if you notice patterns you'd like to change, or if you feel stuck in your approach to relationships, therapy may be a good option. Finding the right therapist can make a meaningful difference in how you experience dating.
How much does therapy for dating challenges cost?
Therapist rates vary, as each therapist on First Session sets their own fees. You can view pricing on each therapist's profile. Learn more about what therapy typically costs and what factors may affect pricing.
How are therapists on First Session vetted?
All therapists on First Session have their credentials verified during the onboarding process. You can learn more about our therapist vetting process and feel confident exploring profiles to find the right fit for you.