I’ve been talking and meeting with this girl for a little over a month now, we’re hitting it off real well, but I am so nervous and rusty I have no idea what’s right or wrong. For starters, I have no idea how to initiate touching. I can tell she wants me to hold her hand and touch and stuff, but I feel so awkward doing it and I have no idea what the right way is to initiate it. Should I ask her or just ease into it and hope she’s OK with it?

We’re staying in Estes, Co, she told me she just wants to explore and I feel bad not planning a whole lot. Should I just go with it and explore or should I have some fun ideas in mind? I got us some snacks as well as champagne and her favorite drinks for the countdown, I’m going to take her to a fun cherry store on the way in, there are a couple of restaurants to choose from for dinner, and I plan on us walking through all the shops when we first get there as part of the “exploring”. Should I do much else?

When it comes to night time, I am completely inexperienced with “night activities”. She’s been talking extra flirtatiously about “stuff” the last couple of days, so I’m fairly certain she’s interested in doing that sort of thing tomorrow night (and the fact that when I suggested a cabin she was all over it within a second of me offerring it), but I am so unnatural and awkward when talking about it, I wouldn’t know what to say or do. I could probably wing it, she’s really easy and fun to talk to, but just the thought of it already has me super nervous. What kinds of pointers do you have to help take the edge off and make it a little more natural? I really like her and would like her to be my “New Years Kiss”, again, I feel so awkward initiating such a thing, is that something I should ask her or just try to read the signs and go for it?

I know even this post is really awkward, but I haven’t had a date in over 4 years and I’ve never been in a serious relationship before. I know it’s pathetic, but I have no idea what I’m doing, so if there is anything else you have to add, I would greatly appreciate it.

6 comments
  1. Don’t focus on what to do physically, just focus on connecting mentally, and the rest falls into place. My husband and I love the Questions for Humans and Questions for Couples card packets that help prompt fun, thought provoking conversations and steamy/flirty moments. If it’s your thing, have a couple drinks in the mix. You’ll find out more about eachother and wants and preferences and have soooo much fun learning about her and yourself. Laughter helps loosen up the nerves and create bonding moments.

  2. Have a few drinks, that can break the ice. If you summon the courage to hold her hand, and do it in a natural way, and you feel she responds nicely, i.e. squeezes back when you squeeze, just pull her to you and kiss her.

  3. Dating hasn’t changed in the past four years. Or really in the last 4 decades.

    She most likely wants you to make a move but there is never any harm in getting verbal confirmation. It can be very sexy to have someone say “I really want to kiss you” or “Is it okay if I kiss you” or to ask after a kiss “was that okay”? Odds are you’re going to get a very enthusiastic response from her.

    It’s also never a bad idea to be prepared so you might want to pack some condoms (although she may do that if she’s hoping things get sexy).

    You can always start with just talking too. “I’m so glad you’re here with me. I really love spending time with you.” If she responds well to statements like that you have a much more natural path into “I’d really like to kiss you.”

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