Matchmaker Says: How To Make The First Move

Original Art by Malika Favre

Original Art by Malika Favre 

One of our NYC clients reached out last week asking for 2nd date tips — as he’s going on a 2nd date with his most recent Tawkify match (huzza!). Specifically, he wanted to know if our experts had any pointers for the following question…

“I like this woman and I don’t want to end up in the “friend zone.” Do you have any tips on touching and/or (more importantly) how to go about making my move on the first kiss?”

We most certainly do have tips! 

Matchmaker Sabrina Yudelson on the subject:

I think touching her arm casually while laughing/making a joke/telling a funny story is the best way to show you are interested and to gauge if she is too. It’s not as intimate as touching her waist or hand, but shows clear interest. If she leans in or does it back, it may be safe to try out a first kiss at the end of the night. Be sure to make eye contact for an extra second or two before going in for the kiss so she isn’t surprised… I’m also a fan of the under the table knee bump/touch.

No footsie, that’s weird.   

Matchmaker Kristina Cappuccilli: 

Here’s my advice: Don’t over think it. If this is your second date with her, chances are she hasn’t placed you in the “friend zone,” and is really looking forward to the next time you hang out. As far as making the first move, go with your intuition.

Recognize her body language and gauge the situation. If it feels right, go with it. As complicated as women seem, we let you know (in our own subtle ways) if we’re comfortable with you making that first move. Be relaxed, be confident, and be yourself.

Matchmaker Christina Han: 

Matchmaker Olivia Balsinger agrees with Christina:

YAAAS Christina. I wholeheartedly agree. It’s also about not overthinking/forcing anything. A kiss or no kiss at the end of the evening does not “seal the deal” or end things, respectively. I have a client in a very similar situation and I always remind him that chemistry talks.

Matchmaker Laura Martin: 

I know many women who feel confused or frustrated at the end of a date when a guy doesn’t make the move. If the date has been going well and you feel a connection, go for it. That lingering moment at the goodbye is always a good time — don’t rush through that part and miss your window. Say goodbye, you had a great time, reach for the hand and if she isn’t rushing away she is most definitely waiting for you to kiss her!

Matchmaker Melody Kiersz: 

I think everything that has been said is great, and I love what Christina and Olivia said especially.

I like when a man asks if he can kiss me. It gives me agency, and I get to say yes if I’m feeling it, which feels like a gift I’m giving…

“I also am a huge believer in guys getting out of their heads and trying to figure a woman out, and to feel into her energy instead. Presence is HUGE, and if he can get out of his own way, he’ll be able to read whether she’s ready or not.”

Plus, just because a kiss doesn’t happen doesn’t mean she isn’t into him. Kissing is pretty intimate, for some more than others, and she might just not be ready to kiss but could be still wanting to explore the connection.

I have a friend who finds kissing more intimate than sex, for example.

Tawkify VP Marketing & Sales (and Certified matchmaker), Michele Presley weighs in:

Personally, I’ve always been partial to the reaching out for the hand, other hand under the elbow, softly and then leaning in from the side for a lingering (just a moment longer than friend zone) cheek kiss after 1st date approach. He’s expressing interest and wants a second date, but isn’t assuming it will happen. It’s an invitation that says so much, but keeps it classy.

Matchmaker Liana Afuni:

Every personality is different – I think the only advice I can give is to be perceptive of a persons body language, let things unfold organically, and respect your date’s boundaries…

“Be mindful that cultural background, as well as dating history could also clue a person into how fast/slow they should move-in expressing interest and intimacy.”

Heartalytics Editor, Valerie Presley Ackler:

I think the majority of this advice can be applied by women as well. We are addressing a specific question from our male client, but why can’t a female make the first move? In fact, this applies to all people — on any kind of date. Engaging in subtle physical touch and expressing clear intention to kiss (or not) is something all daters should take note of, regardless of gender or orientation.

Feeling ready for that 2nd date?


Your Tawkify Matchmakers

For an updated take, read: The 4 Tenets of Pandemic Dating and 5 Reasons To Video Date Right Now

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