25 Questions You Ask Yourself When You’ve Only Ever Had Almost-Relationships


I have been single all my life. It has been an endless cycle of falling and failing.

At the age of 22, I have exclusively dated 5 guys. The first one lasted for a year and a half; the others lasted for 3 to 7 months. None of these became official.

The scenario all seems similar yet different. I meet someone, and then start getting to know them, start spending time with them, and when things are finally hitting off, when it is clear that we both like each other, when I consider that maybe I could take it to another level, I lose them. Three of them left because of another girl, and the other two said they were too busy to be in a relationship. I never really fought for anyone. I never asked any of them to stay. I never asked them to try a little harder. I never felt I had the right to. I never felt I was in the position to ask them to. They weren’t mine anyway. We didn’t have that boyfriend-girlfriend label. I just let all of them slip away, with all my unanswered questions and my hurting heart.

It has been a while since I have dated, and now that I think I’m ready again, I can’t help but ask these questions. The questions that anyone who has ever experienced an almost-relationship will understand.

1. Did he ever really like me?

2. Was there someone else along with me?

3. Was I just one of his girls?

4. Did I really like him?

5. Was I rushing him too much?

6. Was I attached too soon?

7. Am I asking for too much?

8. Did I become too aggressive?

9. Did he really have intentions of taking it to another level?

10. Was I reading all the signs wrong?

11. Was it wrong to expect more than what we had?

12. Was I wrong to believe him when he said he loved me?

13. Were all my efforts not enough?

14. Was I playing it safe?

15. Should I have given him more time?

16. Was I wrong to let him go when he wasn’t even really mine?

17. Should had I fought for him when he said good bye?

18. Am I not good enough?

19. Was I not taking enough risks?

20. Will he stay if I asked him to?

21. Should I have told him how I really felt?

22. Was there anything else I could have done for him?

23. Was it simply not meant to be?

24. Will there ever be anyone who will stay?

25. Will I ever be enough? Thought Catalog Logo Mark

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