Wingman Coaching is Wingman Of The Year’s personalized dating guidance program led by our expert coach, Sophia Bloom. It’s like having your very own wingman (or wingwoman!) who’s also a trained dating coach. In one-on-one sessions, Sophia uses her psychology background and real-world dating expertise to help you navigate the modern dating scene. Think of it as a fun, supportive coaching experience where you get practical advice, learn about yourself, and build confidence to crush your dating goals – all in a low-pressure, judgment-free environment.

Sophia Bloom is our lead Wingman coach – a dating and relationship coach with a strong psychology background and a passion for helping people find genuine connections. She’s studied how the human mind works in relationships and has mentored with top dating experts, blending research-based insights with the kind of real-life dating wisdom you’d expect from a close friend. Sophia’s coaching style is honest yet supportive: she’ll give you kind, no-nonsense feedback (the kind you need to hear) while cheering you on. In short, Sophia is the secret sauce of Wingman Coaching – equal parts knowledgeable professional and your personal dating cheerleader.

If you’re looking to up your dating game or feel more confident meeting new people, Wingman Coaching is probably for you! We work with anyone who wants help navigating dating – whether you’re shy about approaching others, getting back into dating after a break, or just tired of swiping with no luck. At Wingman Of The Year, we believe anyone can use a great wingman, so this coaching is open to all genders and backgrounds (yes, everyone is welcome). If you’re ready to put in a little effort to see big improvements in your dating life, you’ll fit right in. The bottom line: Wingman Coaching is for anyone who’s serious about making dating more fun, fulfilling, and successful.

Expect a casual, conversation-style session that feels more like chatting with a supportive friend – who just so happens to be a dating pro. Sessions are typically one-on-one (usually over a video call, so you can be anywhere) and last around an hour. Sophia will ask questions to get to know you and your goals, and together you’ll dive into whatever dating challenges or topics are on deck. You might go over recent dating experiences, practice conversation starters, or even role-play a first date scenario. It’s all very personalized: Sophia keeps it relaxed and fun, but you’ll also come away with clear takeaways and action steps after each session.

While both coaching and therapy provide personal support, Wingman Coaching is not therapy – it’s more about practical dating strategies and forward momentum than deep therapy work. She isn’t there to diagnose or treat mental health issues; instead, she’s like a mentor giving you guidance, feedback, and exercises to improve your confidence and skills in the dating world. The vibe is more casual and goal-oriented – you’ll talk about real-world dating situations, get honest advice, and tackle challenges together. Many of our clients find coaching more immediately actionable and upbeat than formal counseling, and hey, it’s definitely more fun than your typical therapy session!

Wingman Coaching is geared toward all those real-world dating skills and dilemmas we all face. Sophia can help you build genuine confidence and self-worth so you feel great putting yourself out there. Sessions might cover how to foster self-worth, tips for approaching someone you’re interested in (without the cheesy pickup lines), and ways to overcome dating anxiety or first-date jitters. She can also guide you through refining your most attractive qualities and how to showcase them on dates so you’re showing off the best, most authentic version of you. If you have a pattern of picking the wrong partners or you’re not sure why things haven’t been clicking, Sophia will work with you on understanding your habits and making healthy changes. In short, expect help on everything from flirting and communication to mindset and personal growth – all tailored to your unique situation.

Great question! Wingman Coaching and our Speed Dating events go together like peanut butter and jelly. If you’re attending our speed dating, Sophia’s coaching can help you get the most out of those events. For example, she can prep you beforehand with conversation tips or body language cues so you feel cool and confident walking into a room of new people. Nervous about making a good first impression in those 5-minute mini-dates? Your Wingman coach has you covered with strategies to break the ice and stand out by just being yourself. Coaching is also a perfect follow-up after an event – you can debrief with Sophia about how it went, celebrate matches you made, and troubleshoot any awkward moments. The result: you’ll go into speed dating with a game plan and come out with more insight, making the whole experience even more fun and rewarding.

We all love our friends, but let’s face it – getting dating advice from friends can be hit or miss (and sometimes a little too biased). Having a Wingman coach like Sophia is different because she brings professional insight and an outsider’s perspective that your buddies can’t always offer. It’s like having a best friend who actually knows the science of dating and won’t just say “you’re perfect, don’t change” when you’re looking for real feedback. Sophia will call you out (kindly!) on things your friends might shy away from, and she’ll provide tailored strategies rather than one-size-fits-all tips. Plus, as part of the Wingman Coaching program, she’s up-to-date on all the modern dating trends and red flags. In short, you get honest, expert advice with a fun Wingman vibe – way beyond the usual “just be yourself” texts from your friends group chat.

We’d desire to help people find their true love, but dating doesn’t quite work that way – and we like to keep it real with you. Wingman Coaching isn’t about handing you a perfect partner on a silver platter; it’s about equipping you with the mindset and skills to create your own luck in love. Sophia will help you become the best and most authentic version of yourself in dating, which definitely boosts your chances of finding a great match. Many clients start seeing more positive interactions and better dates after putting in the work. We can say you’ll come out of Wingman Coaching more confident, prepared, and open to finding that connection when it comes knocking.

Getting started is easy and exciting! Click one of the buttons on the page to book a free introductory consultation call with Sophia. In that initial chat, you’ll talk about your dating goals and see if it’s a good fit (no worries, it’s super casual and no pressure). From there, we’ll get you scheduled for your first coaching session. We offer flexible options, so you can try a single session or jump into a multi-session package if you’re ready to dive deep. Before you know it, you’ll be on your way with your personal Wingman coach, leveling up your dating life one session at a time!