You Need Help: Should I Ask My Friend on a Date Even if I Think She’ll Say No?

Q:

Hi humans!!

Got a quick question!

I have a friend who’s in her mid thirties (ten years older than me,) and is the best human.

We’ve both chatted to each other over the years a bunch about our various love lives, which haven’t worked out for a bunch of reasons, and she’s the most switched on, hilarious, supportive friend you could ask for.

At various times I’ve entertained asking her out. I don’t think it would affect our friendship, either it’s a yes (and obv that changes things,) or it’s a kind no and we laugh about it later and carry on.

The thing is… I’m fairly sure she’s not into me. First up is the age difference. I met her when I was 22 and she was 32, which are wildly different life stages. So I was kind of like her gay little sister.

I’m also pretty sure I’m not her type. I’m chubby and adorable and fairly androgynous, and she’s historically been into hot, slender, masculine women.

One time I did make a joke about bringing her flowers which she laughed off and said how sweet I was, so I’m 99.99% certain she’ll only ever see me as a friend.

Which is totally and completely fine, I love her to bits!

The reason I’m asking is I’m reading Michelle Elman’s ‘Selfish Dating’ book and she talks about how we can never really know unless we ask. And I feel like this is low enough risk that I may as well ask? There have also been a few moments where I’ve been like hm. Maybe I’m not one-sided about this.

What are your thoughts? I suspect you’re going to tell me respectfully to let it die 😉 which is probably the plan, as like I said, I love being her friend! It’s just that once in a blue moon I also wonder what it could be like to be more, as we’re super compatible and it’s just kind of great.

xoxoxox

A:

Hi friend!

My very short answer to your question is: do the thing!!

Okay, here’s the long version. I love that reading a book (The Selfish Romantic) has prompted you to look at your life a bit differently. I suspect this is the kind of thing the author was hoping for when she wrote it! I haven’t read The Selfish Romantic, but I totally agree with the idea that “we can never really know until we ask.” In your letter, you go back and forth a bit, saying you’re 99% sure your friend isn’t interested, but then tell us there have been a few moments between the two of you that have made you wonder.

Let’s go through the reasons you gave that you think your friend wouldn’t be interested in dating you. One: your age difference. I agree that if you two were at really different life stages because of your age gap — ie, when you first met and became friends — that would indeed be an important thing to consider. But at this point, it sounds like you’ve moved on from your baby gaydom and you and your friend are more or less in similar places in your life. Especially considering how small the queer dating pool is, it’s not weird at all to date someone ten years older or younger than you. It’s pretty common! Maybe because of when you met, your friend thinks of you as a gay little sister, as you said, and not a potential dating partner. More on that below.

Reason two: type. I don’t want to completely dismiss the idea of people having a type; I for one have historically been into masculine presenting people of all genders, which definitely qualifies for a type. But I also think human sexuality is more complex than people generally believe, and that it is more malleable than people think. I prefer to think of physical types as a loose guideline, rather than a hard and fast rule. It’s also crucial to remember that human attraction and desire are not exempt from the nasty influence of stuff like racism, fatphobia, misogyny, etc. Someone may have tended towards certain types not because they’re only attracted to those people, but because societal norms tell us certain bodies are the most attractive.

Plus, almost every queer person I know (myself included!) has been thrown by attraction to someone unexpected. Just because your friend hasn’t dated someone physically like you (that you know of!) doesn’t mean she might not consider dating you. This is especially true since she knows and loves you as a whole person and isn’t just checking out your physical appearance from across a gay bar.

Reason three, and this is the backbone of your question: what about your friendship? I think this would be a very different scenario if you hadn’t been so clear and confident that your friendship with this person will remain intact and well, even if she doesn’t reciprocate your feelings or feel open to exploring. You write that if she says no, it would be “a kind no and we laugh about it later and carry on.” I can’t think of a more ideal no than that. On this front, I agree with you that asking her if there’s a possibility of dating is relatively low risk. (Side note: I’m also basing this advice on the assumption that both of you are single!)

So if we’ve established that a “kind no” is a potential outcome that you’re comfortable with and that you feel certain that would be how your friend would turn you down, I have some other questions for you: What about if it’s a yes? Or, here’s a possibility you didn’t list: a maybe?

Maybe she really hasn’t thought of you that way, and is still thinking of you a bit like her lil gay sis. She quite possibly will not respond to you asking her out with a declaration about the secret crush she’s been nursing on you or even an enthusiastic yes to going on a date. But, you asking her out might prompt her to reconsider how she’s been seeing you. Maybe she’ll say she wants a bit of time to think about it. Maybe she’ll say she’s not sure, but she’s open to exploring the idea a bit. How do you feel about potentially receiving this kind of response? Does it feel as okay as the “kind no”?

And to take the hypothetical a bit further: what happens if you two try going on a few dates, make out a bit, or even sleep together a time or two, and then your friend calls it off? What if the two of you have a full on relationship, but it doesn’t work out? I think it’s worth thinking those scenarios through, and feeling good that no matter what, you and your friend will treat each other with kindness and respect, even if there are hurt feelings, even if it turns into a situation where one of you — probably you, to be honest — becomes more emotionally invested in a romantic relationship between the two of you. Of course, only you can answer these questions for yourself right now. And if you two dip your toes into dating, these are questions you can discuss explicitly with each other, but where you’ll still have to ultimately make the call about what is right for you.

Good luck my friend and please keep us posted, whichever way it goes!


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Casey

Known in some internet circles as Casey the Canadian Lesbrarian, Casey Stepaniuk is a writer, librarian, and new parent. She writes for Book Riot and Autostraddle about queer and/or bookish stuff. Ask her about cats, bisexuality, libraries, queer books, drinking tea, and her baby. Her website is Casey the Canadian Lesbrarian. Find her on Twitter, Litsy, Storygraph Goodreads and Instagram.

Casey has written 125 articles for us.

7 Comments

  1. good question and good advice!

    but I wasn’t into the “assuming you’re both single” line — maybe “assuming you’re both available to date new people?” because poly people exist, y’know?

    • I think it’s implied since OP doesn’t mention that either are poly and that the advice giver is adding the caveat of singledom for the more general audience, just to remind people that cheating is not condoned!

      I do like your phrase of “available to date new people” because beyond poly, it reminds us that sometimes people aren’t available. They could be having a hard time with a death in the family, or a huge project that consumes all their time. A request for a date during that time would certainly not be ideal.

  2. Asking her out is an option, and so is a conversation letting her know how you feel. The conversation more low stakes in that it’s not a question requiring an answer, but it also is less bold (which can be better or worse). You know yourself and your friend better than we internet people do, so make whatever decision you can live with. Both are options!

    What I don’t recommend is continuing to simmer on this crush unless you are totally fine with nothing ever happening and your crush eventually petering out. Sometimes that’s fun, but it sounds like you want to know what she’s feeling.

  3. Please don’t let an age gap hold you back! I am 15 years older than my gf (44/29) and the gap has never been an issue for either of us. This may change in the future due to aging and health….but maybe it won’t? If there’s a connection and both parties are emotionally mature and respectful of one another, then age shouldn’t really matter. Good luck!

  4. I wish I had this advice in college. I always built up potential crushes in my head SO HARD and was convinced I could never tell them without a clear sign. The confidence of op is lovely to see. So many years later we are all still friends and I wish I had the guts to say something then (not to have anything change) but to know what the outcome would of been instead of wondering every now and then.

  5. Just as a warning, I once told a close, long-time friend that I had feelings for her in a similar situation. I was pretty sure she didn’t feel the same way but confident it wouldn’t hurt our friendship. She gave me the absolute kindest no in the moment and said all these nice things about our friendship. But then a few days later, I realized that she had blocked my phone number and she literally never spoke to me again. So, I’d recommend only asking your friend out if you can handle the possibility that it may end your friendship because that possibility may not be as far-fetched as you think.

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