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The title explains the situation, but there are a couple of details that you need to know about to have a better understanding of the situation:

  1. She (23, hair-dresser and part-time model) and me (24, college student) have been in an on-and-off relationship for 4 years. Although we have often split up and found each other again, we never lost a strong (physical) desire for each other.

  2. Her understanding of a relationship is to go on vacation together. I myself hate "vacation". I would rather travel, but that's not possible with her because she prefers hotels and restaurants over sleeping in the woods and a meal from the supermarket.

  3. She has hinted every day for 8 weeks that she wants to go on vacation with me, repeating the date when she wants to go at least once a day, but always in a rather friendly manner.

  4. She is clearly overworked and states often that staying overseas with me would cure this.

  5. My passion is entrepreneurship and I've been saving my thin student-worker wages to bridge the time of unemployment when starting a startup. This being said, going on holidays would set me back financially quite a bit.

  6. Although I like her very much because she has a very innocent heart, I do not think of her as my future wife. From experience (advice from successful entrepreneurs) I know that a startup rarely tolerates any relationship on the side.

Telling her this, however gentle and respectful, will trigger a very sad / disappointed reaction in her.

The question is therefore: How do I tell her all of this while being as adult and respectful about the situation as possible (what choice of words, what situation, how to behave if she starts a massive guilt-drama)?

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    Even if your relationship has been on-and-off-again; is she truly unaware of the fact that you hate vacationing as she sees it? Does she know you have no plans to commit to the relationship in the future? (You said you don't think of her as a future wife) – user8671 Sep 7 '18 at 8:52
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    There is lack of important context about why explaining her your preference would be an issue. Why do you think this would trigger a “massive guilt drama” from her? – Storm Sep 7 '18 at 9:10
  • Why the downvote? @storm: because this is what happens sometimes when someones expectations of another person are not fulfilled. Not that she is a drama-queen or anything but I noticed that, especially young woman, tend to use guild as manipulative technique – Alon Sep 7 '18 at 12:12
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    Also, how have you responded to her announcement of these holiday plans in the past, and what where her reactions? – user6109 Sep 7 '18 at 12:38
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    Don’t think I down-voted. From your comment it sounds like you are guessing her reactions. How did she actually react when similar conflicts happened in the past between you two? This help the readers understand the background and provide specific actionable suggestions – Storm Sep 7 '18 at 14:24
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I don't think the problem here is the vacation. In fact, you even say that you do like vacations, just a different kind. You appear to like "travelling" and sleeping in the woods; she wants hotels, beaches and exotic locations.

To be honest, it sounds like you are two very different people. Just look at these quotes:

"she prefers hotels and restaurants over sleeping in the woods and a meal from the supermarket"

"She [is a] hair-dresser and part-time model.... My passion is entrepreneurship".

You seem very different in your personalities and have very different goals, which is probably why you also say:

"I do not think of her as my future wife."

I'm not sure if the conversation you ought to have with her should be about why you don't want to go on vacation together, or perhaps why you should break up altogether. But this isn't an advice page. I can only advocate honesty in your conversation, and tell her straight. The longer you string anything out, whether that be her expectation over the vacation or about the relationship altogether, it will hurt her. You do note:

she has a very innocent heart

If you break her expectation over anything it will be bound to upset her, but the longer you leave that, the worse it will be.

You need to talk about all the things you probably never talk about, given the nature of your relationship which you describe as almost entirely physical. "Entrepreneurship" is surely about hard work, but I wouldn't say it excludes any relationship. What we all need, no matter what our goals, is a partner who supports us and shares the same goals. Be careful in this respect - some people with goals like yourself may be pursued by people who think your work ethic will mean access to lots of money. You need to be in a relationship with someone who has the same work ethic as you, not just the desire for the reward.

Ask her what her goals are. Maybe you'll be surprised if you've never really discussed this properly. But if you feel that you are going in different directions, point out these differences to her and tell her how you feel about the longevity of your relationship.

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