I have been in this situation a couple of times and only needed to learn my lesson once. So let´s see if my mistake can be your advantage.
First things first: Common sense. Would you like to meet her and her friend? Going on a wild guess, I´d say you want to see her alone. Furthermore, a “date” should be between two people, unless we went back in time to the 50s.
This does not mean she is not interested, but that is definitely not a date. Would I go to the park with two people, to get to know them? Yes. Would that be a date? NO.
What would I do: What always worked for me was to accept both parties´ boundaries, meaning hers and mine. If she doesn´t feel comfortable being alone with me, I would give her time to get to know me, but not including her friend. I can do this with her friend and a couple of my friends and make a party out of it, but not in that setup.
Furthermore, what worked beautifully for me was always be clear about my intentions. The women I dated knew from the first date that this was a date between two people who liked each other. I´ve got rejected of course, but I never wasted my time nor my money. And I must say that the times I did get dates it worked like a charm.
I like this approach. I’ll be more relaxed if we’re just hanging out. I can ask her out on a DATE in the following days. She’ll be more comfortable and my intent will be spelled out.
I wish I was better at this. I’m unsure where the line between too forward and too reserved is, so I end up being too reserved. What can I tell her to be more clear?
I know a couple of marriages resulting from similar arrangements. My parents ended up together when my mom’s boyfriend insisted on doing a double date with my dad and his current girlfriend. Mom had one dance with Dad and that was all she wrote.
Or just chat with her and say since it is not a date you will probably dress down, like to warn her in case she was going to dress up very nice. Then when she says oh but I thought it was a date you can act very surprised and say how that does not make sense with two girls at the same time.
If she wants bring her friend, just go and see what happens. What harm is it unless you want something quick like sex quickly. If like this and the man is has or I feel this what he wants I would just not go out and go out with my room mate and have a good time.
you seem more engaged with it than some of the ‘experienced’ guys in this thread, so I’d say don’t sweat it, go on date, and try to get a one-on-one next time
i don’t think anyone is as good at it as they would like to be. Fwiw, think Bz’s suggestion is pretty good. I’m pretty reserved about that stuff too. I like to channel it through some other excuse if that makes sense - ala, the Bz or TaipeiGuy examples, which are basically: Well, this isn’t a date, but I do want to go on one. The nice thing about the excuse part is that it forces you to bring out the true part - you’re not gonna say the this isn’t a date part and then fail to follow it with the “but i want to go on one” part.
for me personally the annoying part would be having to entertain both of them at once; it’ll be awkward if you don’t, and if you make it awkward, then both date and friend go home and talk about that and just reinforce the awkward.
Another idea OP could consider is just taking her somewhere very public and comfortable for her? hopefully that might help him dump the friend.
I hope after you made the “date” you stopped texting her or interacting so much. You need to build up excitement and let her think about you before the moment.
Personally, when I was single, I learned to be wary about people wanting to bring a friend, seeing that as a sign of low interest. I would politely decline. “Two’s a company, three’s a crowd.” There’s just SO many women out there.
It’s been a while since I dated, but yeah, what’s the harm in going out with both?
She trusts her friend more than you anyway, so I’d ensure her friend got just as much or more of my attention.
Then both your bases are covered. If nothing comes of it, face is saved. If something happens, cool. If she was trying to pawn you off on her friend, ok, now you know her a bit as well and have that choice.
Btw. I think that calling going out with someone a “date” puts so much unneccessary pressure on that situation. Is that an American thing? Why not just going out with someone or with a bunch of people, without calling it anything but “going out.”
I know she enjoys shopping so I selected the mall, perhaps too comfortable and casual. I will treat this more as hanging out. Low pressure and a fun time. Next time I’ll pick something more intimate.
