[brandy]

Hi April, I know many people ask “is it ok to have sex on the first date?”, however, my question is much more conservative… “should you kiss a man on the first date?” (I mean a “real” kiss). If not, how many dates is a respectable amount of time, without being over the top? I know I’m a bit “old school”, but I’m recently divorced after a very long marriage and never really dated much prior to that. Thank you for you advice.
Brandy

[Ask April Masini]

Well, there’s really no set amount of time one should wait for the first (real) kiss. What I would say is that you should to do what feels right for you. If you are very, very attracted to a man and you feel like kissing him, there’s nothing wrong with that. On the other hand, if you’re unsure about how you feel — definitely don’t… “Thank you” along with a kiss on the cheek, after a date, is appropriate. That said, men do like a chase and if you elect to passionately kiss him on a first date — I would recommend stopping there… with one kiss.

The key is to keep him wanting more.

Desire and wanting… it’s “the wanting” what makes all of us feel alive and it’s what keeps men coming back for more.

Also, just for the record, I am a firm believer that the man needs to be the one who initiates… be that a date, a kiss, a commitment or sex.

[Ethan Morales]

April’s advice here isn’t about arbitrary “rules” it’s about energy management. She’s not saying, don’t kiss too soon or he’ll lose respect. She’s saying: don’t give everything away before desire has space to build.

A first kiss isn’t just about lips it’s about mystery, curiosity, chemistry. When you hold back a little, you’re not playing games; you’re giving that spark room to grow. And when you do finally share that kiss, it means something. That’s the essence of what April calls “the wanting.”

That said, I think it’s equally important to honor your instinct. If you’re with a man, you feel that connection, your heart is racing, and you want to kiss him it’s perfectly fine. There’s no moral line you’re crossing. What matters is that the kiss comes from mutual excitement, not obligation or fear of losing him.

April’s last point that the man should be the one to initiate speaks to an older dynamic of masculine pursuit, which still resonates for many people because it preserves polarity. The man leads, the woman responds. It’s not about power; it’s about rhythm. But even within that, you can signal interest hold eye contact a second longer, smile, step closer. You can invite him to initiate without taking that away from him.

So my take? Don’t kiss him because the “timing” says it’s okay. Kiss him because the moment does. But if you’re not sure yet let him earn it. The anticipation will do half the work for you.

Can I ask, though when you imagine being on that first date again, what would make you want to kiss him? The chemistry, his confidence, how he treats you… or just that magnetic pull you can’t explain?

[Serena Vale]

Brandy,

I think April got it spot-on. There really isn’t a fixed timeline for when that first real kiss should happen. It’s not about rules, it’s about what feels right for you in that moment.

If you’re genuinely feeling the connection and you want to kiss him, that’s okay. And if you’re not there yet, there’s absolutely nothing wrong with keeping it simple, a sweet goodbye, a kiss on the cheek, and taking your time.

And yes, there’s truth in letting a little mystery and anticipation build. You don’t have to rush intimacy to show interest. Sometimes holding back just a bit makes the connection stronger, and the right man will appreciate that and keep showing up.

Trust your pace, trust your instincts, and don’t feel pressured either way. Dating after so long can feel confusing, but you’ll find your rhythm again, and you deserve a connection that feels natural and exciting, not forced. 💛

[Natalie Noah]

You’ve been in a long marriage, you’ve lived a whole life, and now you’re stepping into dating with a tender, curious heart. That already makes you respectful, grounded, and self-aware which matters more than any dating rule. A real kiss on a first date isn’t “too fast” if the connection, safety, and chemistry are genuinely there. But if you’re unsure, hesitant, or still figuring out what you want, then holding back isn’t only okay, it’s beautiful. It builds anticipation, and men actually love that space of wanting.

Let the man initiate, let yourself respond naturally, and don’t force anything you’re not ready for. A kiss should never be scheduled it should feel like a moment you both lean into, not a rule you manage. When the connection is right, the timing will feel right too.

[Author]

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