Many of my clients ask “How do I show that I want to take things further and go on a date?” or “How do I know if my date wants to kiss?” They may have a fear of embarrassment, awkwardness, getting it wrong, harrassing or making the other person uncomfortable. It’s hard to know when the right time is, what to do or say, and what the risk to your friendship or working relationship might be.

Then there’s the challenge of taking it to the next stage after one, two or three dates. When and how can you give a compliment or say you’re attracted? When should you kiss or hold hands? When should you have sex?

I’m really enjoying Season Two of Virgin Island and love Episode 3 on dating, where it’s all about getting in touch with and owning your erotic energy, being present in your body and slowing down. In my coaching work common themes are shame and your relationship with your body, identifying beliefs and emotions – often from our upbringing – about sex and attraction – and deciding what you want to change, and what you want to be accepting of. (These are big themes that aren’t quickly fixed, and may need therapy rather than coaching.)

These principles are foundational to expressing attraction and creating connection or sexual chemistry, so I would suggest investing time in those first.

Practical, easy tips for creating connection

As well as working on these deeply held beliefs, there were on Virgin Island some simple practices the islanders used effectively that you could try too. These included how to use eye contact and body language to create a connection. You’ll need to watch my video to learn more about these and more.

Friends first or friendzoned?

Many people are friends before it turns romantic, despite what you hear about being friendzoned if you don’t create chemistry immediately.

In the new, expanded second edition of my dating workbook, I dedicate a whole chapter to how to find out if there is any potential for romance in a way that reduces the risk of awkwardness or discomfort in either person, with a series of steps and scripts that you can use or adapt.

How do I show I’m interested in someone at work?

This can be risky for a number of reasons and the steps I outline in my workbook will be useful here too. You will need to be more cautious because people want the workplace to be a safe space, so interest is really best expressed outside the work environment. One question could be “How do you feel about socialising with people out of the workplace?” and if they seem positive about that, you could suggest meeting for a coffee or drinks. Then I refer you to the steps in the book!

Creating chemistry on the first few dates

Giving compliments is a good way to show you are confident in what you value and in your own judgement. It also makes the other person feel good about themselves. But most importantly, it’s a way of communicating your desire to connect and your interest in them. Compliments can be about something specific they are wearing, the way they listen, their sense of humour, their personality, their energy and more. Try not to give holistic physical compliments such as “I think you’re hot”: focus on something specific like their shoes, a piece of jewellery, jacket, hair or eyes at this stage.

Expressing attraction is not just about physical attraction. People want to be valued for who they are – especially as these are longer-lasting qualities than appearance. Think about your definition of attraction and what you find attractive in someone that is not physical.

When you message after a date, you could say something like “I really liked … about you on our date”.

How they respond to your compliments may give you some evidence of whether they are interested. If their eyes light up, they make eye contact, thank you and give you a compliment back, those could be green lights to suggest another date or ask if it would be ok to hug, hold hands or kiss.

Expressing attraction after a few dates

Ruth Ramsay, adult sex educator and coach, has some great tips to build sexual connection or express attraction for those who take it slow or don’t have much experience or confidence in this area. She says, “It’s totally normal to feel nervous and shy around expressing attraction if you’re not sure how the other person feels. Even the most confident, experienced people can feel nervous around this! Take a deep breath and know these feelings are normal and ok.”

Ruth suggests, “If you feel too nervous to express attraction face to face, use technology. You can message after a date to say, ‘After we left the restaurant, I wanted to ask if I could kiss you, but I wasn’t sure how you felt and didn’t want things to be awkward. If I’d asked, what would you have said?’ If your attraction isn’t reciprocated, that saves the in-person awkwardness for both of you. Yes the rejection will hurt, and that’s normal. Even the most confident person would feel this. If your date would have said yes to the kiss, it builds the anticipation for the next date, and you can feel much more confident in asking for real.

Ruth advises: “Don’t touch someone without consent. Asking consent can be super-hot. Think, ‘I’d love to hold your hand… would that be ok?’ said softly with a smile. Or you can playfully put the ball in their court: ‘Just so you know, if you wanted to hold my hand, that would be ok with me.’ If there’s chemistry with physical contact, build that sexual connection by maintaining the touch, and with eye contact if that’s comfortable for you. When people are sexually attracted to another person they typically hold eye contact longer than they would with someone they are not attracted to.”

Ruth suggests “Successful sexual relationships are built on communication, honesty and vulnerability. If you are going to go forward into a sexual relationship with this person, you can start creating a template of honesty and transparency right away. Let them know if you feel nervous or feel shy. Let them know if this is a brand-new experience for you. Let them know if ‘I have no idea what you’re thinking right now… Can you help me out?'”

There are more practical tips in my workbook on how to navigate the journey from first date to sexual intimacy and beyond.

When should we have sex?

There’s no right answer to this – you’ll need to talk about it! You can find out more in another post, How many dates before sex?

What if they are not interested?

It can be painful, but you don’t have control over that. All you can do is be your authentic self. Ruth says, “You and your words/actions are only half of the equation. How they react is down to a whole plethora of factors beyond simply whether they fancy you. You can have no way of knowing at this stage what they are. It’s easy for me to write, but try not to take rejection entirely personally.”

I would add that “rejection” isn’t even the right word. You reach out, they decide not to respond. It doesn’t mean your judgment wasn’t good or your feelings weren’t valid. There could be many reasons why they were not interested that have nothing to do with you doing anything wrong. You have value exactly as you are. Sometimes it is worth the risk, even though it is painful.

It might feel as though there are a set of rules that you don’t know about, but mostly no one knows what they are – you’re no different. Each new encounter has its own dynamic, and you have to feel your way around, and look out for what’s going on – or you can just ask directly with a smile and a gentle tone of voice, something like “I really like you and would love to explore whether we could be more than friends. What are you feeling about that?”

Further reading and support on sex and dating

How To Create A Connection On A Date

How many dates before sex?

What to wear and how to smell good: Preparing for a date

How should I prepare for my first date?

Regulating your emotions

Anxious about Dating?

Sex, Dating and Relationships during the Menopause

Video: Sex and dating: your questions answered

Trans dating, sex, identity and relationships

LGBTQ+ sex, dating and relationships resources

Neurodivergent sex, dating and relationships resources

The Joy of Sex by Alex Comfort and Susan Quilliam (50th anniversary edition, published 2008)

Come as You Are: The Surprising New Science That Will Transform Your Sex Life and Come Together by Emily Nagoski

Tell me what you want: The Science of Sexual Desire and How it Can Help You Improve Your Sex Life (2018) by Dr Justin Lehmiller, who is a leading expert on human sexuality and author of the popular blog Sex and Psychology. This book is based on his study of sexual fantasies involving more than 4,000 people from all walks of life.

Great Sex Starts at 50  by Tracey Cox. Practical advice and information about the menopause and changes to the body and relationships, for all sexualities and genders, worth reading before you get to 50 since the peri-menopause starts in early forties

Magnificent Sex: Lessons from Extraordinary Lovers by A. Dana Ménard and Peggy J. Kleinplatz. Magnificent Sex is based on the largest, in-depth interview study ever conducted with people who are having extraordinary sex

She Comes First by Ian Kerner: a witty, well-researched and revealing guide to giving your lover with a vulva an orgasm every time

Queer Sex by Juno Roche – A clear and honest guide that everyone can read to broaden your understanding of how gender has an impact on sexual relations, as well as being a great resource for the trans and non-binary community

How to Understand Your Sexuality : A Practical Guide for Exploring Who You are by Meg-John Barker and Alex Iantaffi. With a new edition for 2021, this is down-to-earth guide to sexuality and how it links to our identities, desires, personal experiences and the world around us, with activities and reflection tasks

Sex in the Digital Age (2018) edited by Paul G Nixon & Isabel K. Düsterhöft

The Course of Love by Alain de Botton

The Kiss Quotient by Helen Hoang

Bridgerton Series 1-3 on Netflix for healthy sex scenes

Sex coach and educator Ruth Ramsay for coaching programmes and workshops

Ruth’s TED talk on sex

Your Midlife Libido: Where It Went And How To Get It Back

OMGYes

Podcasts for body acceptance and-positivity

Sex in films

Justin Lehmiller’s podcast Sex and Psychology

Erotic blueprints

Pleasure Portraits on Instagram and the book Pleasure Portraits by Emma Halenko

The Great Wall Of Vulva online plastercast exhibition of over 400 vulvas by Jamie McCartney

The photography of Laura Dodsworth with her 100 penises and 100 vulvas books

My husband wants more enthusiasm from me


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