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Tero Vesalainen/Dreamstime/TNS

5 top tips for dating in 2025

Life Advice / Dating Advice /

After 13 years of helping people find love (and sometimes dodging a few bullets along the way), I’ve seen the dating landscape evolve dramatically.

Let’s look at five tips for navigating the dating world this upcoming year.

1. Curate your dating profile like it’s a first impression (because it is)

Your dating profile is your personal ...Read more

DREAMSTIME/TNS

Should we have 'the talk'? When? How?

Life Advice / Dating Advice /

Question: “I have been dating someone for three months, and we’re exclusive (not seeing other people). I’m ready to define the relationship (DTR) but don’t want to lose him if he’s not ready. How to have the talk?”

My response:

“For better or for worse (and I hope better, of course!), that's a risk you're going to have to take. I...Read more

Irina Viatokha/Dreamstime/TNS

Who invited your ex on this date?

Life Advice / Dating Advice /

I received this text from a client I started working with recently: “I really want to solve this issue of people mentioning their exes! Or maybe that’s just normal if you’re divorced? Is it me? Or does that happen to other clients on every single first date? It’s so uncomfortable!”

And then this week, after a different client went on ...Read more

Syda Productions/Dreamstime/TNS

No holiday plans? This social app will match you with a group of strangers for dinner

Life Advice / Dating Advice /

LOS ANGELES -- When David Brown moved from Chicago to Los Angeles this summer, one of the first things he did was download an app that aims to "fight big-city loneliness."

The 35-year-old sales director had seen an Instagram ad for Timeleft, which matches users with strangers for dinner via a personality algorithm. Since he only knew a handful ...Read more

Golubovy/Dreamstime/TNS

Ask Anna: Help! My boyfriend's gift game is weak -- here's how to talk about it

Life Advice / Dating Advice /

Dear Anna,

When it comes to gifts, my boyfriend of two years kinda phones it in. For my birthday last month, he gave me a gift card to a coffee shop, which was sweet, but I work from home and don’t even drink that much coffee! Last Christmas, I got a generic piece of jewelry that wasn’t my style at all. I’ve tried to tell myself it’s ...Read more

Anton Estrada/Dreamstime/TNS

How much should I tell my friends about my love life?

Life Advice / Dating Advice /

It’s 11 p.m. on Tuesday, and you’re wrapping up a first date. And it was a pretty good one! It ends with a hug goodbye and tentative plans to get together again for dinner early next week (you know, if you ever hear from him again). As you climb into your Lyft and give a final wave to your date, you’re excited that after a string of "mid" ...Read more

Elena Titova/Dreamstime/TNS

How do you know if someone is ready to date?

Life Advice / Dating Advice /

Question: “How do you ask if a guy is ready for a relationship if he is ripe off of a five-year relationship?”

This is a question I received recently, and I get some form of the “How do I know if someone else is ready?” question quite frequently.

My response:

“People are notoriously bad at self-assessing their readiness. The only ...Read more

Benzoix/Dreamstime/TNS

Ask Anna: How to handle being single during cuffing season without losing your mind

Life Advice / Dating Advice /

Dear Anna,

Usually Mariah Carey season is my favorite, but this year I’m struggling. Everywhere I look, people are cozying up, planning cute holiday dates and posting about their jolly AF lives. Meanwhile, I’m single, spending my evenings scrolling through dating apps and wondering if I should just settle for someone mediocre so I’m not ...Read more

 

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