How to suggest more than friendship?

[rr88]

A while back I met a woman at this volunteering group that we were both going to. It was all quite laid back and outdoorsy, it was a good way to meet new people who enjoy hiking and the outdoors.

Neither of us go very regularly to it anymore but we started hanging out occasionally just the two of us. We've been on a couple walks around the park and out for a couple of meals.

I'm quite happy being friends with her, but I'm also quite attracted to her.

I've always felt like we've been merely 'just friends' though mainly because she is absolutely stunning – I'd have thought a woman like her was way outta my league and that she probably just sees me as a really 'trustworthy friend' rather than relationship material.

But I also wonder if its a good sign that she's happy meeting me 1-on-1, even if it is mostly me who suggests it... and there's also sometimes several weeks between us meeting.

I've also found in recent years that some surprisingly-attractive women have showed an interest in me, which makes me wonder if I'm more attractive that I realised... I can still be a little shy around women though

Would it be an idea to just message her and just be really clear about it? e.g. saying that I find her attractive and wondered if she'd like to go on a date?

Should I also point out that I wouldn't want it to ruin our friendship if she didn't feel the same way?

[Cherylyn]

I wouldn't message her.  Wait until you see her IN PERSON.  Tell her what you've written,  be humble,  very honest and sincere.  In person is best.  Messaging (texting) can often times not have the reaction you're anticipating.  In person is always best.  Meet for coffee or lunch or something like that.  Perhaps a walk or something?  Remember, in person is best!  It's far more effective and you're more likely to receive a positive outcome instead of a negative one.

[boltnrun]

I agree, do not hide behind an electronic device. Sure, you might think it would sting less if she rejects you via typed message but if any man liked me and wanted to date me I would not be impressed if he asked via a typed message on some device. I would think he lacked basic social skills at the very least.

Ask her for a date. Call her or ask her the next time you meet up for a walk. Say something like "I really enjoy spending time with you. I would love to take you out to dinner. Would you like to join me for dinner at Nice Restaurant Thursday night?" Do NOT say "wanna grab some food?" because that sounds like a friendly hangout. Make it clear you want to take her on a date.

Good luck!

[waffle]

40 minutes ago, rr88 said:

. . . saying that I find her attractive and wondered if she'd like to . . 

 

8 minutes ago, boltnrun said:

Say something like "I really enjoy spending time with you. I would love to take you out to dinner . . . "

Please note the difference in wording between these two approaches.

[Kwothe28]

I think you missed "the window of opportunity". Once they see you as a "trusted friend" you are forever in the friendzone. That is why you position yourself better at the start and not as a chit-chat buddy for once in a blue moon talks. Because now she see you as a friend and not as an object of interest for a relationship. You are "non-threatening" individual to her. Meaning that she doesnt mind going out with you for a coffee. But wont ever be with you as she doesnt even look at you as a "boyfriend material". Sorry.

Lots of people think if the just gravitate there it would lead to some relationship. I am sure some did make it from there but in 99% of cases, no, it just doesnt happen. You need to clearly express your interest. And not be "buddy-buddy" with her and then try something. 

But, in spite of all that, I do urge you to at least try. Express your interest and take her to a proper date. You clearly like that girl which means you cant be friends no matter what happens. So, take her to dinner, pay her a few compliments and see how she reacts and go from there. 

[Wiseman2]

1 hour ago, rr88 said:

Would it be an idea to just message her and just be really clear about it? e.g. saying that I find her attractive and wondered if she'd like to go on a date?

Do not blurt anything out in a message. Just plan a more romantic style date and hold hands or something. The reaction or what she says will tell you all you need to know. 

[Batya33]

Definitely ask her out in person.  I volunteered for years at a homeless shelter and for about a year or so a guy also volunteered.  Around my age.  We went the same direction after so a few times we walked to the bus stop together and a few times we chatted during the hour or so we were there. Nice person.  I would have gone on a date with him had I been available.  I wasn't and definitely mentioned my boyfriend and did not flirt.  I was surprised he still seemed to be "pursuing" me but I simply stayed friendly.  He stopped likely because he met his future wife!  But -point is -yes if I'd been single I'd have been open to seeing him one on one. I mean I wasn't insanely attracted to him but sure I'd have given it a chance!  So give it a chance!

[DarkCh0c0]

1 hour ago, Kwothe28 said:

But wont ever be with you as she doesnt even look at you as a "boyfriend material". Sorry.

We don't know that for sure.

OP, definitely ask her out over the phone or next time you meet.

Follow 100% what @boltnrunadvised. That's a tactful way to ask her out.

[Andrina]

First things first, you can't guess who another person will find attractive or not, nor who they will have chemistry with. Just do your best in keeping up with a haircut and clothing that looks best on you. You'll either be someone's cup of tea or not. I have found certain men attractive but did not feel chemistry, which is biology. I also don't need a man to look like a model, but have to find something that wows me about his face, like striking eyes. Some women like the banker/businessman look. I like the construction worker look. What people find attractive is very individual and runs a wide gamut.

Next, don't tell a woman she's attractive when asking her out. It's a given you do find her attractive and that's why you're interested. Nothing that should be said at that point. Save the compliment for when you pick her up for the date, and she's dressed up. Something like: "Oh, you look so pretty. Love your dress."

Like Bolt said, make it clear it's a date by the venue. If she doesn't want to lead you on and doesn't want to date you, she'll likely hem and haw and maybe let you know she's not interested in going in that direction.

If she happily agrees with no hesitation, it's a good sign.

Do not throw in the "We can still be friends even if you say no." For one thing, that sounds too doormat-like, and that it comes from someone with low self-worth.

You won't want to hear this because you're high on spending time with her, but it's really not a good idea to stay friends with her if she's not interested in dating. And I don't mean to cut her off cold if she chooses not to date as a punishment. It means that you should let that new friendship fade away, and don't let it grow, because believe me, it's going to hurt a potential romance you have in the future.

Women are intuitive, and believe me, a new woman you're trying to date will ask about this stunning woman friend, i.e., "You two never dated? Why not?" You will then  either have to lie, which isn't ethical, or tell the truth that you would have liked that, but the woman wasn't interested."

I'm sure you haven't thought that far ahead, but believe me, you should.

I hope she says yes, and if she does, don't let your idea that she's out of your league sabotage something good. Start believing you're worthy or other people will think, "Oh, he thinks he's a pile of crap. Maybe he is, since he knows himself better than anyone else." See how your mindset affects your life to a great extent? Something you can work on.

Good luck and let us know how it goes.

[Coily]

I agree with the with the others, you need to know.

Make some nice plans, get yourself in a positive mindset and ask her out. Leagues are garbage, people find someone they like, not who is the best set of statistics.

if you don’t ask, you will have this regret over your head. Not ideal.

[catfeeder]

I'd follow Bolt's advice and just ask her out for a date. I would not lay some pent up confession on her. Just call your dates dates, and allow rather than force your discussions to evolve.