How to approach asking a longtime friend out?

Question

Some context is due. We've known each other for more or less 9 years now, from our late teens and now nearing our late twenties. We both lead rather busy lives, so especially throughout the past few years, we tended to fade in and out of each other's lives. This more or less depends on whether we happen to be single or not.

A couple of months after we initially met, during our college years, I did ask her out but she thought otherwise. Nonetheless, we remained good friends, and have supported each other a lot through these 9 years.

For the past few months now, we've been hanging out quite a bit, certainly more than we have in the past couple of years. Perhaps, those initial feelings of so many years ago are resurfacing again -- but I don't know if that is okay, after so many years of friendship.

There are, perhaps, some red flags which I feel I should point out. I have always sought her advice on relationship matters [I am quite introverted and shy when it comes to these matters]. Certain things she says I should look out for, vis-à-vis signs of interest, I seldom see from her. But, then again, I personally think that they are out of her character -- but let's say we don't assume that.

How would you approach this matter, while being respectful to 9 years of friendship and trust?

Answer 1

I wound up marrying someone I had been friends with for a while, so perhaps my experience can help.

Let's start with the risk here. I was worried that if I took things too far, I'd lose years of friendship from someone who meant a lot to me. I think you face that risk here as well. You need to decide first if that risk is worth it.

Let's say you decide it is. The next thing is to determine if there is interest from her for the same thing. Luckily in my case, she was pretty upfront about that. Unfortunately, as a group, women are way more subtle than men are so things that they think are obvious are anything but obvious to us. She may be sending some signals one way or the other that you aren't picking upon. Looking back at my dating life, I missed a LOT of signals from women - both positive and negative. So be aware that she may be telling you something already that you haven't picked up on.

You've been hanging out - that was what did it for us. Is it just you or are you hanging out with others? If it hasn't been just you, then I'd suggest taking that step and hang out as friends and see where that takes you.

At some point, you'll both need to define the relationship (Mormons call it the "DTR Talk" - Define The Relationship, as I understand.) You'll want to know where you stand and so will she. I'd suggest doing that after a time or two of hanging out together. Be honest with her - you asked her out a long time ago; does she still feel the same way? What do you have to offer her? Hint: "You're single and so am I" is NOT going to win points here. You enjoy hanging out together - does she want to do that? What is she looking for romantically? Is she out of the dating market for a while? Is she coming down off a relationship? This is a minefield you are walking into and it's important to understand the map before you set off something you can't take back.

In my case, marrying an old friend has been incredibly rewarding and I can't imagine NOT being friends with my wife. Physical attraction changes, you both gain weight, your interests change, but if you have a good friendship you can weather those storms together. The important thing is to be open and honest and accept whatever she decides.

Answer 2

I’ve been in a similar situation as you. I met one of my closest friends when we were younger and we hit it off pretty well. Initially it definitely felt as though we had an attractive bond. Ultimately I ended up with someone else though and those feelings were never pursued.

We both have been in and out of relationships as time went on and have been there to support each other through it.

I have always wondered what it would be like to see if we could work together; to pursue those feelings we had.

But I’ve come to realize that through time, people change. Not only that, I also figured that this time we haven’t dated is also in it of itself a possible descriptor for why we haven’t further pursued anything.

So I think before you ask it is very important to really consider why you haven’t dated already. She could have realized that she really values your friendship now and never would want to risk losing it. The thing about meeting someone sooner, is time is on your side. It wouldn’t be as tragic and painful if things didn’t work out. The bonds haven’t been thoroughly developed yet.

How would you approach this matter, while being respectful to 9 years of friendship and trust?

I think once you decide to ask this it will have a big impact on your relationship regardless of how it is phrased.

Once you ask, the friendship you have is at risk of becoming an awkward situation if she doesn’t reciprocate those feelings. She may constantly feel bad knowing you have feelings for her but she does not. You would put her in a difficult place and it may be overwhelming.

Regardless, I recommend you really consider everything before asking, as this can be a real life changing decision. Maybe even ask mutual friends that you can trust to see how she feels about you. These trusted people could really be helpful in determining their feelings when it’s difficult to read their subtle hints.

Once you are sure you are going to ask just be open about how you feel. Describe how your friendship is really important to you and how you wouldn’t want to lose it. Go on to say you’re interested in pursuing a more romantic relationship given how well you’ve connected over the years.

Just be natural and don’t stress it. If you’re really nervous beforehand, just practice in your head how you’ll phrase it. It can really be helpful to think about the phrasing beforehand, as feelings and emotions can be especially tricky to describe.