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.
Stephanie Neshcov
Registered Psychotherapist (Qualifying)
Virtual Sessions in ON, YT, NT, NU, BC, AB, SK, NL, MB, NS, QC, and NB.
Waitlist
Stephanie Neshcov
Registered Psychotherapist (Qualifying)
She/Her
Anxiety, Stress, Life transitions, Boundaries and boundary setting, Building Self-Care Routines, Dating challenges, Depression, School challenges, Relationships, Workplace stress
Anxiety, Stress, Life transitions, Boundaries and boundary setting, Building Self-Care Routines, Dating challenges, Depression, School challenges, Relationships, Workplace stress
Samudyatha Hiremagalore
Registered Clinical Counsellor
Virtual Sessions in AB, BC, NB, and ON.
Waitlist
Samudyatha Hiremagalore
Registered Clinical Counsellor
She/Her/Hers
Break-up recovery, Attachment, Relationships, Couples, Conflict resolution, Cultural Challenges, Dating challenges, Deep connections, Family issues, People pleasing, Separation and divorce, Abuse (Sexual/Physical/Verbal), BIPOC
Break-up recovery, Attachment, Relationships, Couples, Conflict resolution, Cultural Challenges, Dating challenges, Deep connections, Family issues, People pleasing, Separation and divorce, Abuse (Sexual/Physical/Verbal), BIPOC
Michèle Dawn
Registered Therapeutic Counsellor
Virtual Sessions in all provinces and territories.
Waitlist
Michèle Dawn
Registered Therapeutic Counsellor
She/Her
Anxiety and Stress Management Skills, Nervous system regulation, Emotional regulation, ADHD, Anxiety, Attachment, Boundaries and boundary setting, Break-up recovery, Blocks in Connecting with Self and Others, Burnout, Building Self-Care Routines, Career guidance, Creativity, Dating challenges, Decision making, Goal Setting, Life transitions, Low Self-Esteem and Self Worth, Mindfulness, Imposter syndrome, Overwhelm, Stress, Wellness Counselling, Negative thinking and ruminating, Habits
Anxiety and Stress Management Skills, Nervous system regulation, Emotional regulation, ADHD, Anxiety, Attachment, Boundaries and boundary setting, Break-up recovery, Blocks in Connecting with Self and Others, Burnout, Building Self-Care Routines, Career guidance, Creativity, Dating challenges, Decision making, Goal Setting, Life transitions, Low Self-Esteem and Self Worth, Mindfulness, Imposter syndrome, Overwhelm, Stress, Wellness Counselling, Negative thinking and ruminating, Habits
Shane Pokroy
Registered Psychotherapist
Virtual Sessions in ON.
Waitlist
Shane Pokroy
Registered Psychotherapist
Self-Development, Empowerment, Mental performance, Mindfulness, Overwhelm, Motivation, Perfectionism, Goal Setting, Stress, Burnout, Productivity, Relationships, Anxiety and Stress Management Skills, Negative thinking and ruminating, Career guidance, Dating challenges, Existential questions, Decision making, Couples, Creativity, Emotional regulation, Habits, Imposter syndrome, Life transitions, Men's issues, Meaning and purpose, Nervous system regulation, Spirituality
Self-Development, Empowerment, Mental performance, Mindfulness, Overwhelm, Motivation, Perfectionism, Goal Setting, Stress, Burnout, Productivity, Relationships, Anxiety and Stress Management Skills, Negative thinking and ruminating, Career guidance, Dating challenges, Existential questions, Decision making, Couples, Creativity, Emotional regulation, Habits, Imposter syndrome, Life transitions, Men's issues, Meaning and purpose, Nervous system regulation, Spirituality
Crystal Soares
Registered Social Worker
Virtual Sessions in ON.
Waitlist
Crystal Soares
Registered Social Worker
She/Her
Attachment wounds, Intergenerational trauma, Boundaries and boundary setting, Relationships, Dealing with difficult or narcissistic personalities, Trauma, People pleasing, Self-esteem, LGBTQ2IA+, Blocks in Connecting with Self and Others, Perfectionism, Overwhelm, Childhood trauma, Familial and social relationships, Anger, Anxiety, Attachment trauma, Dating challenges, Assertiveness, Break-up recovery, Depression, Attachment, Understanding & Regulating Emotions, Social anxiety, Sexuality
Attachment wounds, Intergenerational trauma, Boundaries and boundary setting, Relationships, Dealing with difficult or narcissistic personalities, Trauma, People pleasing, Self-esteem, LGBTQ2IA+, Blocks in Connecting with Self and Others, Perfectionism, Overwhelm, Childhood trauma, Familial and social relationships, Anger, Anxiety, Attachment trauma, Dating challenges, Assertiveness, Break-up recovery, Depression, Attachment, Understanding & Regulating Emotions, Social anxiety, Sexuality
Terence To
Registered Social Worker
Virtual Sessions in ON.
Waitlist
Terence To
Registered Social Worker
OCD, Anxiety, Depression, Anxiety and Stress Management Skills, Career guidance, Dating challenges, Fears and phobia, BIPOC
OCD, Anxiety, Depression, Anxiety and Stress Management Skills, Career guidance, Dating challenges, Fears and phobia, BIPOC
Meagan Gallacher
Registered Psychotherapist (Qualifying)
Virtual Sessions in ON.
Waitlist
Meagan Gallacher
Registered Psychotherapist (Qualifying)
She/Her
Addiction, ADHD, Adoption, Attention and Impulsivity, Anger, Anxiety, Anxiety and Stress Management Skills, Borderline Personality Disorder, Break-up recovery, Building Self-Care Routines, Dating challenges, Boundaries and boundary setting, Depression, Emotional regulation, Effective communication, Goal Setting, Low Self-Esteem and Self Worth, Infidelity, School challenges, Mindfulness Practices, People pleasing, Phobias, Self-esteem, Abuse (Sexual/Physical/Verbal)
Addiction, ADHD, Adoption, Attention and Impulsivity, Anger, Anxiety, Anxiety and Stress Management Skills, Borderline Personality Disorder, Break-up recovery, Building Self-Care Routines, Dating challenges, Boundaries and boundary setting, Depression, Emotional regulation, Effective communication, Goal Setting, Low Self-Esteem and Self Worth, Infidelity, School challenges, Mindfulness Practices, People pleasing, Phobias, Self-esteem, Abuse (Sexual/Physical/Verbal)
Lisa Schwartz
Registered Social Worker
Virtual Sessions in NS and ON.
Waitlist
Lisa Schwartz
Registered Social Worker
she/her
Anxiety and Stress Management Skills, Children/Teens, Familial and social relationships, Adjusting to a diagnosis, Attachment, Boundaries and boundary setting, Break-up recovery, Building Meaningful Connections, Dating challenges, Childhood trauma, Family Conflict, Highly Sensitive Person, Navigating challenging relationships, Parental divorce, Parenting, Meaning and purpose, Life transitions, Low mood, People pleasing, Self-esteem, Workplace stress, School challenges, Grief and Loss, Identity and Self-Exploration
Anxiety and Stress Management Skills, Children/Teens, Familial and social relationships, Adjusting to a diagnosis, Attachment, Boundaries and boundary setting, Break-up recovery, Building Meaningful Connections, Dating challenges, Childhood trauma, Family Conflict, Highly Sensitive Person, Navigating challenging relationships, Parental divorce, Parenting, Meaning and purpose, Life transitions, Low mood, People pleasing, Self-esteem, Workplace stress, School challenges, Grief and Loss, Identity and Self-Exploration
Michael Appiah
Registered Social Worker
Virtual Sessions in ON and BC.
Waitlist
Michael Appiah
Registered Social Worker
Relationships, Men's issues, Effective communication, Anxiety and Stress Management Skills, Workplace stress, Assertiveness, Attachment, Career guidance, Christian counselling, College or University Coaching, Dating challenges, BIPOC, Cultural Challenges, Decision making, Conflict resolution, Couples, Low Self-Esteem and Self Worth, Self-Development, School challenges, Imposter syndrome, Anger Management
Relationships, Men's issues, Effective communication, Anxiety and Stress Management Skills, Workplace stress, Assertiveness, Attachment, Career guidance, Christian counselling, College or University Coaching, Dating challenges, BIPOC, Cultural Challenges, Decision making, Conflict resolution, Couples, Low Self-Esteem and Self Worth, Self-Development, School challenges, Imposter syndrome, Anger Management
Paula Fernández
Registered Social Worker
Virtual Sessions in ON.
Waitlist
Paula Fernández
Registered Social Worker
She/Her
Wellness Counselling, Dating challenges, Identity and Self-Exploration, Adjusting to a diagnosis, Anxiety and Stress Management Skills, Assertiveness, Attachment, Boundaries and boundary setting, Depression, Family issues, Mindfulness Practices, Life transitions, People pleasing, Self-esteem, Relationships, Transformative dream work, Spirituality, Trauma, Understanding & Regulating Emotions, Workplace stress, Women's Health, Grief and Loss
Wellness Counselling, Dating challenges, Identity and Self-Exploration, Adjusting to a diagnosis, Anxiety and Stress Management Skills, Assertiveness, Attachment, Boundaries and boundary setting, Depression, Family issues, Mindfulness Practices, Life transitions, People pleasing, Self-esteem, Relationships, Transformative dream work, Spirituality, Trauma, Understanding & Regulating Emotions, Workplace stress, Women's Health, Grief and Loss
Erica Berman
Registered Psychotherapist
Virtual Sessions in all provinces and territories.
Waitlist
Erica Berman
Registered Psychotherapist
She/her
ADHD, Adjusting to a diagnosis, Aging, Anger Management, Anxiety, Anxiety and Stress Management Skills, Assertiveness, Attachment wounds, Boundaries and boundary setting, Break-up recovery, Building Meaningful Connections, Body Dysmorphia, Building Self-Care Routines, Burnout, Career guidance, Childhood trauma, Coming out and identity, Conflict resolution, Couples Therapy, Cultural Challenges, Dating challenges, Depression, Effective communication, Emotional regulation, Abuse (Sexual/Physical/Verbal), Couples
ADHD, Adjusting to a diagnosis, Aging, Anger Management, Anxiety, Anxiety and Stress Management Skills, Assertiveness, Attachment wounds, Boundaries and boundary setting, Break-up recovery, Building Meaningful Connections, Body Dysmorphia, Building Self-Care Routines, Burnout, Career guidance, Childhood trauma, Coming out and identity, Conflict resolution, Couples Therapy, Cultural Challenges, Dating challenges, Depression, Effective communication, Emotional regulation, Abuse (Sexual/Physical/Verbal), Couples
Daisie Auty
Registered Social Worker
Virtual Sessions in ON.
Waitlist
Daisie Auty
Registered Social Worker
she/her
ADHD, Relationships, LGBTQ2IA+, Adjusting to a diagnosis, Anxiety, Assertiveness, Attachment, Break-up recovery, Burnout, Coming out and identity, Complex Trauma (CPTSD), Emotional regulation, Dating challenges, Familial and social relationships, Family issues, Neurodiversity, Intergenerational trauma, Parenting, Relationship anxiety, Low Self-Esteem and Self Worth, Sexuality and gender issues, Self-Criticism, Understanding & Regulating Emotions, Workplace stress, Identity and Self-Exploration
ADHD, Relationships, LGBTQ2IA+, Adjusting to a diagnosis, Anxiety, Assertiveness, Attachment, Break-up recovery, Burnout, Coming out and identity, Complex Trauma (CPTSD), Emotional regulation, Dating challenges, Familial and social relationships, Family issues, Neurodiversity, Intergenerational trauma, Parenting, Relationship anxiety, Low Self-Esteem and Self Worth, Sexuality and gender issues, Self-Criticism, Understanding & Regulating Emotions, Workplace stress, Identity and Self-Exploration
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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.