If a man asks me to fly out to see him should I expect him to pay?

Wife_and_Mama · 2026-02-18T01:54:41+00:00

I think the real question should be whether or not you should go.

My expectations of what will come of seeing him are uncertain.

You don't even know the goal here, his or yours. Are you planning to sleep with him? Because he's absolutely expecting it. If not, are you okay with this being a one-time thing for a romantic weekend or will you feel used? If you're okay with it, then what? Do you keep in touch? Do you hope to have a real relationship one day? I wouldn't suggest going in the first place, but if he invites you and you're happy to be his weekend fling, I definitely wouldn't suggest you pay for the opportunity.

SkinnyJeans44 · 2026-02-18T01:29:11+00:00

'' FMTY '' Fly me to you is a term often used in the high class escort industry. If you think that's whats going on here then he should absolutely pay. If it's not , i think you should pay yourself but if i were you i would just decline the offer. You dont know what your expectations of this interaction should be. Try chatting with him to gauge what his expectations are of this visit. Is it a high end booty call or does he want to pursue you romantically as well.

LightOverWater · 2026-02-18T01:39:46+00:00

I mean, people can arrange things however they'd like but...

Typically the man pursues and flies to you (safest for you). Else, he can pay to fly you there if that's his request. You bear the risk. It's a bit weird to request that an acquaintance (you) spends $1,000. He should pay.

If this is your idea, you'd pay. And you'd probably be deeper into a relationship if that were the case. Alternatively, both travel to meet somewhere else.

Thick_Emu_3516 · 2026-02-18T03:26:02+00:00

I think he should come visit you and stay in a hotel. I think you should say something like:

I'm attracted to you, but I've often felt you were looking for a grand romance rather than a real life relationship. If you want to consider a relationship, come visit, stay at the Hilton and spend some platonic time with me. We can run errands, walk the dog, you can meet my friends...I want to see how we feel in the real world not a Caribbean vacation.

This is how you determine whether he likes the idea of you, or actually wants to get to know the real you.

LoonerMoth · 2026-02-18T02:26:10+00:00

The real issue isn’t so much if he’s paying or not, but if he’s willing to take turns flying to you. Flying is a hassle, and if he’s always putting this hassle on you, chances are he’s kind of lazy and selfish or just doesn’t care that much to see you. For a man with some money, purchasing a ticket is the easy part.

Overall, this is sending up a lot of red flags to me, especially him asking you to move with him right away when you were 19. And the fact you’re questioning if the image he’s projecting is legit probably means it’s not.

AphroditesNightie · 2026-02-18T23:09:07+00:00

I agree that you need to decide what your motivation is for going to see him before you go. I think he should pay for the flight if you go.

Just as a cautionary tale: Years ago I broke up from a long term relationship, and had stayed in touch with a (male) friend from high school over the years (he is just a friend - not an ex boyfriend). At the time, that friend called to say he was coming back to our home state to visit his family. He had moved across the country a few years before that. He invited me to come and spend a weekend at his mother’s gorgeous (and huge) beachfront home while he was staying there. Since I also knew his mother when we were kids, and he said there was an extra bedroom for me, I was comfortable doing that and agreed. I had not seen him in years and I definitely thought it was just going to be a fun weekend at the beach, catching up with an old friend and his mother. It wasn’t too far from where I was living, so transportation wasn’t really an issue. What shocked me was that this old “friend” took this opportunity to confess that he had always been in love with me and wanted to be more than friends. Unfortunately, I did not… It was very awkward after he confessed this on the first night I was there. I think that’s when it really sunk in that the famous line from When Harry Met Sally was absolutely true: Men and women can’t be friends because sex always gets in the way.

If he wants you to fly to the Caribbean to see him, he is most likely expecting more than just a friendly visit. You have to decide if that’s what you want.

annie_kingdom · 2026-02-19T11:51:35+00:00

I was in similar to different situations. I let things flow without asking or clearing things out. BIGGEST REGRET OF MY LIFE!!!!!!!!!!!!!!!!!!!! Everyone later blamed me that I did not communicate clearly from the start with him of what my expectations from the meeting up of the trip. If you are afraid to ask or he wont give clear/direct answers. Then, YOU state what you want from him. Make it clear. Do not regret it, I did.

SolutionDecent · 2026-02-18T01:31:43+00:00

Yes. Immediately yes should pay.

AutoModerator · 2026-02-18T01:24:00+00:00

Title: If a man asks me to fly out to see him should I expect him to pay?

Author FanOk2082

Full text: I’m talking to a guy (32) who I was once intimate with when I was 19. He’s messaged me a few times a year since then. I’m now 26. I never fully entertained him. Most of this time, I’ve been in a long term relationship.

He’s very attractive, has an interesting job, and comes from a wealthy family.

He’s asked me to visit him 3 times in the last few years.

The first time was when I was 21. He didn’t offer to pay.

The second time a flight wasn’t on the table as I was driving down to his city with some friends but didn’t get to see him as wild fires ended our road trip short.

And the third time was last year when I broke up with my now ex for a brief period before reconciling. Me and him were living together, so he offered that I stay with him while I got things situated with the break up.

We have started speaking recently and I suspect that he will ask me to visit him again. He’s currently in the Caribbean.

My expectations of what will come of seeing him are uncertain. He’s very charismatic and I question if he’s as great of a guy as he seems to be from the conversations that we’ve had, or if he’s just good at projecting that image. So visiting him would be to get to know him better and explore a possible connection.

If he acts me to see him, should I expect him to pay?

If I should, do I suggest that he does if he doesn’t offer up front?

Or considering the fact that I don’t know where this will go, and leading with the idea that I don’t have any expectations, just an awareness of different possibilities; a romantic relationship, or a good friendship, do I get the ticket myself?

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Antique_Mountain_263 · 2026-02-18T03:18:42+00:00

Is he from where you live? Maybe he could visit home sometime?

You could meet up for lunch, activities, dinner, etc and get to know him again on your terms. Where you can safely go home when you wanted to. And say goodbye at the end of the night and go to your home, so you don’t feel pressured to sleep with him.

I would not recommend planning to spend the night with someone that you haven’t seen in years. Especially not in another country.

Do you know his family, any of his friends? Ask about him. Is he into sketchy stuff? The “interesting career” might be a potential red flag.

The love bombing is a concern. It’s hard to tell if it’s genuine or not.

I can tell from your responses you are wondering if it would lead to a possible serious relationship. Definitely make the expectations about a relationship clear up front before any visits are planned.

I wouldn’t waste time with guys who don’t want to get married.

Do you have any relatives around that you trust to open up to about this? Ask for their input too. Ask your dad what he thinks.

BudgetInteraction811 · 2026-02-20T22:15:22+00:00

Never ever let a guy fly you out. That’s escort-adjacent behaviour and he’s doing the same to other women. If a man is intentional about you, he will take the time off to come visit you.

Regardless, what kind of man asks you to fly to meet him but doesn’t buy the tickets? That’s even more tactless. Don’t waste another minute on this guy; stick to dating locally.

Plenty_Cellist_4885 · 2026-02-24T04:25:05+00:00

If what you want here is to see if he is relationship material, then you have to show yourself in the same frame to see that side of him. So if he asks you to visit and you want to visit, then just tell him sure and "go ahead and book it." If he books it, just say thank you. If he balks,, then you know there's absolutely nothing worth entertaining here, he doesn't respect you (has money, wants you to fly to see him, expects you to pay airfare, that's a no.) But if you agree to go you need to be clear on why you're going. So before you do say sure ask questions about where you'll sleep, does he have "room" for you. That way you can avoid sleeping with him on this visit by lowering his expectations before you even get there, because again, you're looking to evaluate him for relationship potential, not be some lady he flies in whenever he's had a dry spell. That's the real test because if he does pay for you to come after hearing you ask for separate sleeping quarters, and then you do come and don't sleep with him, then the aftermath of all that will start to tell you how serious he is. If he's more interested after the trip, then maybe he is relationship material. And if he isn't then he'll probably pout and ignore you afterwards. So look at this like your experiment to figure out if he's worth your time.

VasiliyZaitzev · 2026-02-18T06:04:25+00:00

My expectations of what will come of seeing him are uncertain.

He doesn't want to fly you down there to just look at you.

If he asks me to see him, should I expect him to pay?

Absolutely, signed, a guy who has flown girls in to meet him.¹ That said, girls I fly in know what's up, so if sex is not on the table for you, but you still want to go, that's when you buy your own ticket.

Here is your decision matrix:

A. "I am going to have sex with him." - he buys.

B. "I am NOT going to have sex with him." - you buy.

C. "I am not sure if I am going to have sex with him." - figure this out before you go, then proceed to A or B, accordingly.

If you are still in category B, you may also want to arrange your own accommodation, to draw a clear boundary.

If I should, do I suggest that he does if he doesn’t offer up front?

Ask if he can "help you" with the plane ticket. He should figure it out from there.

Or considering the fact that I don’t know where this will go

Are you going to sleep with him? Likely to? Because I would bet he thinks you are.

Good luck and proceed accordingly.

= = = = =

¹ This has always, that I can recall, been with girls I have had sex with before, and typically they are traveling for my convenience and ideally flying non-stop or 1 stop - I enjoy travel, even the inconvenient parts, and, as a man an experienced traveler, I am in a better position to handle IRROPS with aplomb, so I prefer to be the one traveling. I used to date a girl who liked to take PTO and then fly to wherever I happened to be. She would fly out of a regional airport, so options for her return were somewhat limited. I would send her back on the morning flight from the West Coast and not the afternoon one. She protested that she wanted to spend that day with me, too, but, when I pointed out that I would rather have her walking alone in the parking garage at 4pm rather than 11pm, she looked at me and said, "You really do think of everything." Think what you want about my lifestyle, but I do take care of my girls.

Title	If a man asks me to fly out to see him should I expect him to pay?
Author	FanOk2082
Upvotes	6
Comments	25
Date	February 18, 2026 1:24 AM UTC (5 months ago)
Subreddit	Posted in /r/RedPillWomen
Original Link	https://old.reddit.com/r/RedPillWomen/comments/1r7p5li/if_a_man_asks_me_to_fly_out_to_see_him_should_i/
Archive Link	https://theredarchive.com/r/RedPillWomen/if-a-man-asks-me-to-fly-out-to-see-him-should-i.1573716 https://theredarchive.com/post/1573716

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