I’ve been speaking to this wonderful girl for about 7 months now and we both want something more, I know that because we’ve discussed it. We talk about everything and anything and I really love it.

The reason I haven’t asked her out yet is because I want to wait until her birthday (Oct) to ask to make it special.

I want to learn more about her past, but I’m worried she’s going to think I’m digging into things or asking too personal questions- it’s mainly stuff like ‘How long ago was it that you split with your ex’

Do you think it’s creepy and odd to ask that? If not; what’s the best way I could ask her? Word it properly so it doesn’t come across weird

TL/DR: I want to ask my girlfriend about her past but am scared it’ll come off strange

8 comments
  1. October is so far away! You’ve been talking for a really long time too. What are you scared of or waiting for?! It’s not going to be special after dragging it out a few more months. I’d be pissed if you deliberately waited that long.

    Also there’s no reason to know how long ago she split with her ex as far as I can see. What would be the benefit of asking that?

  2. Don’t wait until October. She will spend the next 3-4 months wondering why you don’t like her enough to ask her out. She will doubt herself and you as relationship material. She won’t find it special you waited that long. She will find it agonizing.

    Ask her out now. Then just do something special for her for her birthday.

    Then wait a few months into the relationship to ask all the questions you want.

  3. 7 months is a long time to be flirting without asking someone out! Do you live far away from each other? Do you know she split with her ex before she started talking to you?

    Then you call her your “girlfriend” – I’m confused.

  4. If I was talking to a guy romantically for 7 months and he hadn’t asked me out by now, I would assume he doesn’t want anything more and I’d find someone else. Plain and simple. Every day is a special occasion. Don’t wait for it to be too late. October is so far away!

  5. Don’t do it on her birthday because if she’s not interested then you’ll ruin the day. If she means something to you, then just do it. It’s not a marriage proposal.

  6. This is some of the strangest stuff I have ever seen. In your post history you refer to her as your partner. Here you call her your girlfriend after saying you haven’t asked her out and aren’t planning to for months.

    Have you met in real life?

  7. It feels too personal because in many ways, she’s still a stranger to you. Then, for some odd reason, you plan to keep it that way until October. You said that as if it’s perfectly logical, but it isn’t. In fact, it comes across as if you’re reluctant to meet her in person. It’s also possible she’s reluctant to meet you.

    This might be what you want to focus on.

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