Aug 18, 2026 · 27 min · 13 segments
How much information do you actually need before you make a decision in your dating life? In this episode, I’m answering four real dating dilemmas that all come down to that one question. We’re…
I had two dates with both of them at about the same time, but I'm not currently able to see the 40-year-old because he has his kid with him and he's going out of town for 10 days.
But he's being very consistent with staying in touch via text and was very open about wanting to see me again after his trip.
I've since seen the 41-year-old once, and I have another date with him scheduled, and we've progressed to kissing and cuddling.
I like both of them, and I'm not yet sure if the 41-year-old is aligned enough with me to say that I want to see him exclusively.
But I'm worried I'm leading the other man on because I'm starting to catch feelings for the 41-year-old.
I also haven't discussed exclusivity with either one yet, but I've never dated two men at once other than first dates.
I'm wondering if the only reason I'm catching feelings for one over the other is because I haven't been able to see the other in person, and I'm worried that I might miss out if I tell the 40-year-old that I'm moving on.
Do I say something to the one who's traveling? To both of them? How do you navigate dating two men who are both appealing?" All right.
Especially as connections grow, like, technically, I think it's fair to say that if you've not discussed exclusivity and just only seeing each other, there's no issue on paper about seeing multiple people just, you know, for dates.
For your situation, I don't think there's anything wrong with seeing the guy who is traveling after he gets back for a third date.
It's only been 10 days, right? Even if you're on your fourth date with the 41-year-old who you've progressed to kissing and cuddling with.
Try that on mentally, right? If that doesn't sit well with you, then you know your answer, right? You can decide to white-knuckle through it and just be uncomfortable and do it anyway.
I don't like it, so I'm going to make a choice." So let's talk about the fear of missing out on a great connection and calling it off too soon in this scenario.
And I want to remind you that every time you commit to one person, you are saying no to everyone else if you're monogamous.
So is it really a huge loss if you end up choosing a great person and saying no to everyone else? No.
If you feel like you're ready to just focus on the 41-year-old who you've been seeing more often, go for it.
Who you are meeting up with for dates isn't really any of their business at that point.
When I was multi-dating, I never said anything about seeing other people unless someone asked me, because bringing it up when you're still deciding, right, you don't know what you're doing, doesn't go anywhere positive.
Let's play this out, right? Let's say I'm on a date with you, and I'm seeing multiple people.
I had two dates with both of them at about the same time, but I'm not currently able to see the 40-year-old because he has his kid with him and he's going out of town for 10 days.
But he's being very consistent with staying in touch via text and was very open about wanting to see me again after his trip.
I've since seen the 41-year-old once, and I have another date with him scheduled, and we've progressed to kissing and cuddling.
I like both of them, and I'm not yet sure if the 41-year-old is aligned enough with me to say that I want to see him exclusively.
But I'm worried I'm leading the other man on because I'm starting to catch feelings for the 41-year-old.
I also haven't discussed exclusivity with either one yet, but I've never dated two men at once other than first dates.
I'm wondering if the only reason I'm catching feelings for one over the other is because I haven't been able to see the other in person, and I'm worried that I might miss out if I tell the 40-year-old that I'm moving on.
Do I say something to the one who's traveling? To both of them? How do you navigate dating two men who are both appealing?" All right.
Especially as connections grow, like, technically, I think it's fair to say that if you've not discussed exclusivity and just only seeing each other, there's no issue on paper about seeing multiple people just, you know, for dates.
For your situation, I don't think there's anything wrong with seeing the guy who is traveling after he gets back for a third date.
It's only been 10 days, right? Even if you're on your fourth date with the 41-year-old who you've progressed to kissing and cuddling with.
Try that on mentally, right? If that doesn't sit well with you, then you know your answer, right? You can decide to white-knuckle through it and just be uncomfortable and do it anyway.
I don't like it, so I'm going to make a choice." So let's talk about the fear of missing out on a great connection and calling it off too soon in this scenario.
And I want to remind you that every time you commit to one person, you are saying no to everyone else if you're monogamous.
So is it really a huge loss if you end up choosing a great person and saying no to everyone else? No.
If you feel like you're ready to just focus on the 41-year-old who you've been seeing more often, go for it.
Who you are meeting up with for dates isn't really any of their business at that point.
When I was multi-dating, I never said anything about seeing other people unless someone asked me, because bringing it up when you're still deciding, right, you don't know what you're doing, doesn't go anywhere positive.
Let's play this out, right? Let's say I'm on a date with you, and I'm seeing multiple people.
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