Dating at any age requires strategy, boundaries, and a whole lot of confidence. 

But when your best matches aren’t just in a different neighborhood, they’re in a different time zone, a different state, or a different country, the stakes get even higher. Being intentional about love matters even more when your matches aren’t in your backyard.

A listener named Maryanne wrote in:

“I’m 71 and looking for a long-term partner. I read your book and know what’s important to me. I went on two niche sites and matched with a few good options, but they all live elsewhere. I live in San Francisco. I have spent a good amount of time getting to know them by phone and FaceTime. I’m not sure how to proceed with the next steps. One lives in Hawaii and he invited me over for a week. The other guy lives in LA and both seem serious about me. There is even a guy in Mexico who looks interesting who has come on the scene just after the other two. What’s the best way to meet out of town dates? Do I stay in a hotel nearby? Do I insist they visit me? How do I know who pays for what? When do I tell them I am also meeting other men?”

(02:00) Your Dating Pool Has No Zip Code

One of the most powerful things dating apps have done is blow up the old rules about proximity. Census data from the 1930s showed that people typically met partners within five blocks of their home. That era is long gone.

For later daters especially, this shift matters enormously. Local dating pools can be smaller, and the options that exist might not align with your values, your lifestyle, or where you are in life. 

Casting a wider net isn’t settling. It’s smart strategy.

That said, there are ground rules for anyone new to long distance dating:

• Matching and messaging is not dating. Until you’ve met someone face to face, you’re still in the screening phase, no matter how many late-night FaceTimes you’ve had.
• Video chat is non-negotiable. Seeing someone live and in real time is a critical step before any travel gets planned.
• The timeline matters. From the moment you match, you should be moving toward a video call or in-person meeting within one day to one week. Don’t let things linger in text-land indefinitely.

(07:30) Eight Weeks Changes Everything

Long distance connections can move faster and feel more intense than in-person ones. 

Without the natural pacing of regular dates, things quickly turn into nightly FaceTimes, marathon phone calls, and a very real emotional investment in someone you’ve never actually been in the same room with.

That intensity can feel like connection; sometimes it is, but it can also be a fantasy.

The dynamic shifts when you’re physically in the same space. Sometimes for the better. Sometimes not. Either way, you need that information before you’ve made a significant emotional investment.

Staying in the virtual phase too long means you risk:

1. Building up an idealized version of someone that reality can’t match
2. Making major life decisions based on a connection that hasn’t been tested in person
3. Getting so emotionally attached that you overlook things you’d catch face-to-face

If you can meet sooner, do it. Eight weeks is a ceiling, not a goal.

(12:00) Questions to Ask Before You Pack a Bag

Long-distance dating involves real investment, financial, emotional, and sometimes logistical. Before you commit to traveling to meet someone, there are a few conversations worth having first.

What would “working out” actually look like?

If the trip goes well and you decide you want to keep dating, what’s the plan? Is there a realistic path to eventually being in the same place? Who would move, and on what timeline? You don’t need firm answers, but you do need to know if both people are even open to exploring those questions.

Watch for these red flags before you go:

• Pressure to commit before you’ve even met. Grand statements about your future together should raise an eyebrow, not melt your heart.
• Vague non-answers when logistics come up. “We’ll figure it out when you get here” is not a plan.
• Resistance to any questions about their actual life, goals, or lifestyle.
• No real interest in ever meeting in person.

Excitement is not the same as compatibility. It’s wonderful to feel curious and wanted. We just want to make sure what’s underneath that feeling is real.

(15:30) Always Have an Escape Hatch

This is where we get practical.

Do not plan to stay at their house. Not for a first in-person meeting. Not even if they have an amazing setup, it would save money, and everything feels perfectly fine. You need a place that is fully yours.

Having your own hotel room means:

• You have somewhere to decompress and get centered
• You’re not beholden to his space, his schedule, or his mood
• You can leave if anything feels off, without it becoming a whole situation
• You’re not setting up a dynamic where someone feels owed something because they covered your accommodations

As for who pays: you should have agency over where you sleep. They can contribute to the hotel, split the airfare, but you control your lodging. 

Frame it simply and warmly. “I’m so excited to come to Hawaii. I’d feel most comfortable staying at a hotel nearby for this first visit.” That single sentence communicates enthusiasm, sets a clear boundary, and leaves the door open for a next time. How he responds will tell you a great deal.

One more option worth considering: bring a friend. Traveling with someone you trust takes the pressure off the first meeting for both of you, gives you a built-in support system, and makes the whole trip worthwhile regardless of how things go.

(19:00) You Don’t Owe Anyone Your Whole Story Yet

You are not exclusive until you have explicitly agreed to be exclusive.

In the discovery phase, before anyone has even met in person, there is no obligation to account for every conversation you’re having. 

Transparency is a value. Oversharing before there’s even a real relationship to protect is just anxiety in disguise.

The moment the conversation becomes necessary is when you’ve met someone in person, you’re continuing to see them, and you sense they may be assuming something you haven’t agreed to. Or you feel a pull toward one person and want to be honest about where things stand.

When that moment comes, keep it simple: “I want you to know I’m talking to other people as I figure out what’s right for me. I’m being intentional about this process.” No justification needed. No convincing anyone. It’s just where you are.

Around that same eight-week mark, things often clarify on their own. Stay honest with yourself and the rest follows.

We’ve seen long distance connections lead to some of the most profound changes in people’s lives. 

People who never considered moving to a new city. People who had written off the idea of finding love at this stage. People who thought their options were limited and discovered they were anything but. 

What they all had in common: they stayed present instead of projecting into the future, protected themselves while staying genuinely open, and were willing to get on a plane before they had all the answers. 

Sometimes it just takes one meeting to send your life in a direction you never saw coming.

💌 Navigating long distance connections, figuring out who pays for what, or wondering how to date multiple people with honesty and intention? Send your question in a DM or voice memo on Instagram, TikTok, or Facebook, or send a voicemail or text to 424-246-6255. It might just be featured in an upcoming Dear Damona segment.

And remember: Dates & Mates covers all the relationships that matter in your life: romantic partnerships, friendships, family dynamics, work relationships, and most importantly, the relationship you have with yourself.

📝 Ready to track what’s working (and what’s not) in your dating life? Download the free Date Tracker at damonahoffman.com/datetracker. It helps you see patterns and move forward with clarity