How To Make Yourself More Dateable

Expert advice to be successful at dating.

By Sasha Gonzales        30 November 2022

Dating can be tricky – it’s not always easy to tell if your date wants an exclusive relationship or if she’s even the best match for you. It can also be nerve-wracking trying to plan the perfect date and making sure you both hit it off right away. 

The good news is that you can eliminate the stress associated with dating new people, and feel more confident and comfortable when it comes to getting to know a potential partner and letting her see the real you. 

We asked dating and relationship experts, Carita Wong, Life and Wellness Coach at Table for Two, and Cindy Leong, Founder of The Relationship Studio, to share their best tips for improving your dating skills so that you’re sure to snag a second date. 

Make a positive first impression

“First impressions matter,” says Carita.

“Show up to your date looking clean and neat. Do you need to shave or groom your beard? Do your nails need a trim? Remember to wear a fragrance-free or lightly scented deodorant if you perspire easily. Don’t overdo the aftershave in case your date doesn’t like the scent. Dress appropriately for the venue and occasion – ideally, wear anything that makes you look smart, relaxed and confident. Finally, if you have a well-toned physique, avoid wearing a tight-fitting shirt. You want your date to be drawn to your personality and also leave a little to her imagination.”

While waiting for your date to arrive, don’t spend time on your phone, as this might make her feel less-than-important. Carita says that you also want to be ready to greet her when she approaches.

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Be thoughtful – plan a date she won’t forget

Find out what your date’s dietary preferences are, and pick a place that caters to both your dietary requirements, but that’s also cosy and conducive to conversation, Carita suggests. 

The day before, send her a simple message like “I’m excited about seeing you tomorrow” – this is basic courtesy and lets your date know that the meeting is important to you.

Don’t stress about the date, says Cindy. Remember to have fun – there should be laughter and a sense of playfulness and familiarity. 

During the date, ask her what she wants to drink and avoid commenting on the prices. 

“I don’t recommend any physical touch on the first date,” says Carita. 

“At most, if the date went well, a light touch on the small of her back as you’re leaving, to signify “Ladies first”, could be a nice gesture. And please respect your date and the occasion by switching your phone to silent mode and putting it away. Placing it face-down on the table is not good enough.”

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Keep the conversation light but meaningful 

Suitable topics of conversation include hobbies, travel, food, movies, and trends, says Cindy.

“Talk about what drives you both at work and in life, reveal what you were like as kids, and share minor regrets or disappointments and discuss what you learnt from them, as vulnerability draws people closer together,” adds Carita.

Pay attention to your date’s responses and use the responses to segue into other topics.

“When you’re first getting to know someone, avoid discussing certain topics, like exes and your dating history, because you’re both trying to move forward, not back,” says Carita. 

“Don’t discuss sex, either, no matter how physically attracted you are to each other – it’s more important to establish a deep connection. Politics and religion should also be avoided, as these topics may trigger a heated argument.   

“And don’t discuss family dramas, because you’re on a date, not having a counselling session. Finally, a first date isn’t a good time to bring up topics like money, income, and marriage plans – it’s too soon, so save it for when you know each other better and can see a future together.”

Manage your expectations

It’s tough, but try not to have any expectations during the date, says Carita. It’s more important to be present with the person you’re with, to focus on the experience and enjoy the moment, rather than fixate on what you want to happen down the road. Use this time to get to know your date, pay attention to her likes and dislikes, and prioritise her needs. If the date goes well, suggest a second outing before you part ways. Say something like, “Thank you for the lovely time. You’re fun to be around and I’d like to take you out again”. If she responds positively, suggest something she expressed an interest in during the conversation, then say you’ll call her in a day or two with some concrete plans.

After a few dates, it’s fine to discuss where you both see things going so that you can tell if your expectations are aligned with hers, Cindy adds.  

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Be honest about what you want

“Communicating openly is important,” says Carita. 

“It prevents assumptions, which may lead to misunderstandings and unnecessary hurt. It’s best to be clear and honest about what you want when dating. You may get rejected, but at least you found out sooner rather than later. 

“It’s the same if you’d prefer to just date casually but not enter into a long-term relationship. The kind thing to do is not lead your date on. It’s best for both of you to know where you stand with each other and are in a position to choose.

“Deliver this honesty with compassion, kindness and integrity. The intention to be honest must come from the desire to shed light on the truth, alleviate pain or suffering, or resolve a misunderstanding.”

Learn the signs that your date isn’t serious about you

There are ways to tell if the person you’re interested in doesn’t feel the same way, says Carita. 

If she’s still active on dating apps, if she doesn’t consider you when making plans, if she hasn’t mentioned you to her best friends, if she’s not very communicative when you’re not together, and if you’ve noticed that her initial enthusiasm has waned dramatically, then it’s possible she may not be serious about you.

Being aware of these signs may save you the trouble of pursuing a relationship with the wrong partner. 

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