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.

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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.

Andras Lenart

Canadian Certified Counsellor
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Offers In-Person (Victoria, BC)
Virtual Sessions in all provinces and territories.
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Andras Lenart

Andras Lenart

Canadian Certified Counsellor
$170/session
Relationships, Self-Development, Social anxiety, ADHD, Anger, Blocks in Connecting with Self and Others, Motivation, Low Self-Esteem and Self Worth, Dating challenges, Meaning and purpose, Couples Therapy, Emotional Numbness, Anxiety, Decision making, Deep connections, Fears and phobia, Existential questions, Men's issues, People pleasing, Perfectionism, Productivity, Sexuality and gender issues, Psychedelic therapy, Personal Growth, Emotional Fluidity
Relationships, Self-Development, Social anxiety, ADHD, Anger, Blocks in Connecting with Self and Others, Motivation, Low Self-Esteem and Self Worth, Dating challenges, Meaning and purpose, Couples Therapy, Emotional Numbness, Anxiety, Decision making, Deep connections, Fears and phobia, Existential questions, Men's issues, People pleasing, Perfectionism, Productivity, Sexuality and gender issues, Psychedelic therapy, Personal Growth, Emotional Fluidity
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Caitlin Black

Registered Psychotherapist (Qualifying)
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Offers In-Person (Toronto, ON)
Virtual Sessions in ON.
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Caitlin Black

Caitlin Black

Registered Psychotherapist (Qualifying)
She/Her/Hers
$175/session
Self-Development, Couples, ADHD, Borderline Personality Disorder, Dating challenges, Family issues, Mindfulness Practices, People pleasing, Postnatal Care, Separation and divorce, Neurodiversity, Grief and Loss
Self-Development, Couples, ADHD, Borderline Personality Disorder, Dating challenges, Family issues, Mindfulness Practices, People pleasing, Postnatal Care, Separation and divorce, Neurodiversity, Grief and Loss
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Margarita Iarovaia

Registered Psychotherapist
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Offers In-Person (Toronto, ON)
Virtual Sessions in all provinces and territories.
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Margarita Iarovaia

Margarita Iarovaia

Registered Psychotherapist
She/Her/Hers
$150/session
Trauma, Sexuality, Relationships, Sex therapy, Abuse (Sexual/Physical/Verbal), Boundaries and boundary setting, Building Self-Care Routines, Dating challenges, Relationship anxiety, Sexual issues, Trauma processing, Understanding & Regulating Emotions, Mindfulness, Identity and Self-Exploration
Trauma, Sexuality, Relationships, Sex therapy, Abuse (Sexual/Physical/Verbal), Boundaries and boundary setting, Building Self-Care Routines, Dating challenges, Relationship anxiety, Sexual issues, Trauma processing, Understanding & Regulating Emotions, Mindfulness, Identity and Self-Exploration
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Cassandra Fezzuoglio

Registered Social Worker
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Offers In-Person (Vaughan, ON)
Virtual Sessions in ON.
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Cassandra Fezzuoglio

Cassandra Fezzuoglio

Registered Social Worker
She/Her
$185/session
ADHD, Attachment, Anxiety, Anxiety and Stress Management Skills, Attachment wounds, Attachment trauma, Boundaries and boundary setting, Building Self-Care Routines, Break-up recovery, Childhood trauma, Career guidance, Dating challenges, Couples, Competitive anxiety, Emotional regulation, Goal Setting, Imposter syndrome, Negative thinking and ruminating, Health anxiety, Depression coping skills, Navigating challenging relationships, Infertility, Vulnerability, Separation and divorce, Neurodiversity
ADHD, Attachment, Anxiety, Anxiety and Stress Management Skills, Attachment wounds, Attachment trauma, Boundaries and boundary setting, Building Self-Care Routines, Break-up recovery, Childhood trauma, Career guidance, Dating challenges, Couples, Competitive anxiety, Emotional regulation, Goal Setting, Imposter syndrome, Negative thinking and ruminating, Health anxiety, Depression coping skills, Navigating challenging relationships, Infertility, Vulnerability, Separation and divorce, Neurodiversity
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Viktoria Vigh

Registered Social Worker
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Offers In-Person (Mississauga, ON)
Virtual Sessions in ON.
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Viktoria Vigh

Viktoria Vigh

Registered Social Worker
She/her
$180/session
ADHD, Adjusting to a diagnosis, Anxiety and Stress Management Skills, Assertiveness, Autism Spectrum Disorder (ASD), Blocks in Connecting with Self and Others, Boundaries and boundary setting, Break-up recovery, Building Meaningful Connections, Building Self-Care Routines, Burnout, College or University Coaching, Dealing with difficult or narcissistic personalities, Dating challenges, Decision making, Effective communication, Giftedness Issues, Learning disabilities, Nervous system regulation, Self-Regulation, Sleeping difficulties, Neurodiversity, Attention and Impulsivity
ADHD, Adjusting to a diagnosis, Anxiety and Stress Management Skills, Assertiveness, Autism Spectrum Disorder (ASD), Blocks in Connecting with Self and Others, Boundaries and boundary setting, Break-up recovery, Building Meaningful Connections, Building Self-Care Routines, Burnout, College or University Coaching, Dealing with difficult or narcissistic personalities, Dating challenges, Decision making, Effective communication, Giftedness Issues, Learning disabilities, Nervous system regulation, Self-Regulation, Sleeping difficulties, Neurodiversity, Attention and Impulsivity
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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.
About 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.