Dear Dr. Darcy
I've been seeing this woman who's older than me for the last 7 months. We've never done anything and we haven't even kissed. She's never been with a woman but she's been with men which makes me feel a little uncomfortable. She waits for me to make the first move but I don't know how to treat her cause I've never been with an older woman before. I really want to ask her out and finally make a move but should I talk to her first (I'm not a good talker) or just kiss her which I think would make things easier?
I have to confess to being completely confused by your question. You say you’ve been seeing an older woman for 7 months, which to me implies that you’ve had some sort of intimate relationship with her, yet you haven’t even kissed, she’s never been with a woman before, and somehow she magically knows that you’re interested in her and she’s communicated to you (without words) that she’s waiting for you to make the first move? You have a friend. A straight friend, at that. A straight friend who is an older woman (I’d love the quantification of this, btw) and because she’s older, you hesitate to make the first move which is why, for 7-months, you’ve remained friends. These are the facts. The rest of the words that are contained in your question are confusing because they veil these facts in a blanket of vagueness.
Yes, I’d say a conversation would be appropriate, unless you’re planning on remaining in this holding pattern indefinitely. I’d start by confirming that she’s attracted to you, that she’s open to this, and then I’d want to know what this is. Does she want a one time experience, does she want to experiment more than once, or is she interested in dating women? Once you know the answers to these questions, you’ll be equipped to decide if you’d like to pursue something with her. Right now you’re wallowing in a world that is vague, and quite frankly, it’s making me crazy. Get some clarity and make a move.