Throwaway because this contains a bit more personal info than I’d like on my main.

I (26m) first went out with my fiancé Sean (25m) when my (at the time) best friend Ruby (his sister) told me that he was super lonely and asked me to go out with him because I was the only gay guy around his age that she knew. Well, I owed her a major favor and also kinda felt bad for him (to put it bluntly, he had no friends), so I agreed and asked him to the movies. Honestly I was a bit scared of him, he’s 6’5” and muscular while I’m only 5’9” and not what you’d call athletic. I figured I’d go on one date then let him down gently. He said yes, and we, surprisingly, had an amazing time. It went so well, I actually ended up going back to his apartment and getting shitfaced while playing uno with him. Turns out, in spite of the height difference and his social anxiety, he’s a great guy and very sweet once he opens up. Long story short, it’s four years later and we’re getting married in a month.

Yesterday, Ruby came to me and asked me what Sean thought of the fact that our first date was because she set us up out of pity. I admitted that I hadn’t told him because I didn’t see the point. She then told me that I was being cruel by not telling him, and told me that I had a week to tell Sean or she would tell him herself. She framed it like she was exposing a scandal and I have no doubt that she’d spin it to make me look like a liar who led him on or something. There’s a reason she’s not my best friend anymore, we only talk now because of Sean.

The problem is, Sean hates being pitied. Yes he’s tall and athletic, but he’s also extremely shy and introverted, and on top of that he missed a lot of school due to an illness and accident back to back (the latter of which resulted in him losing a leg). As a result, throughout highschool he had zero social interactions (his words) and his social skills were pretty stunted when we first went out. Anyway, according to him the pity from teachers and former friends was always the worst part, and he can’t stand being pitied to this day. I’m terrified to tell him about the circumstances of our first date, because I’m nervous it would make him see me differently and/or damage our relationship. I love this guy, legitimately one of the best humans I’ve ever met. I’d hate for this all to blow up in my face because I didn’t just tell him earlier.

39 comments
  1. Don’t tell him. There’s no reason too. Sure maybe it did start by a pitty date, But that doesn’t matter anymore. If you know it will upset him then keep it to your self. This is a need to know thing and he does not need to know.

  2. I don’t think this is all that uncommon. A friend sets you up with someone that you don’t think you click with, but you try anyways and it goes great.

    If you do tell him, this shouldn’t be a major deal. Some part of you was curious to begin with, or you wouldn’t have agreed at all.

    I don’t think you need to say “you were a pity date” and nor does this have to be some serious conversation. It’s almost humorous imo.

    I think you’re good man.

  3. What is she even thinking?!? Were you nasty about him at the time? Were you particularly disparaging or something? What’s the big deal?

    Sit him down and tell him that his sister set up you up on the first date and at that point you’d only gone out with him because his sister asked you.

    Tell him that and that for some reason his sister is now making out like its a big deal and has threatened you about it – but it really isn’t a big deal.

    You were set up, you weren’t sure about it all, you went on a date – you got on and fell in love. Let’s be honest, if people only dated people they were immediately attracted to, half the people in the world wouldn’t exist. Love isn’t a lightening bolt, it grows like an oak tree.

  4. She’s trying to cause drama. If you can have a conversation with her that all this is going to do is hurt his feelings and make him feel bad. Is that what she really wants? Or is she jealous? Is she actually Sean’s friend?

    Why would you ever tell him this? Why?

  5. She’s trying to sabotage your relationship because you aren’t friends with her anymore. You either tell the truth, get rid of all the information that she can bring up that would show it’s true and then become a great liar. Really only two options.

  6. >getting shitfaced while playing uno with him

    Excellent euphemism for sex.

    Anyway, if you want to beat her to the punch, a not-terrible way to do that is to say that when you first met him you thought he was going to be one type of person (using all of the terminology that you used about his size), and then you were surprised that he was another type of person and that’s who you fell in love with.

  7. This Ruby chick is stirring up drama. She’s his sister? Why is she doing this? Why would she intentionally try to cause issues in her brothers life.

    If he truly loves you, this situation will not hamper his love for you. If she is actually gonna tell him, just beat her to it. Be like “Babe when we got set up with each other, I wasn’t really sure how everything was going to turn out, I didn’t want to go on the date, but Ruby said you were cool. When I spent time with you, everything made sense.”

  8. Bruh, congrats first of all.

    Secondly, if this were me I would take the news well if you said something like “Hey, the first time we went out, I only went because your sister felt bad for you and asked me if I would hang out with you. I didnt think we would click, but we did. I am glad I took that chance and went on a date with you that night.”

  9. The friend is trying to cause drama. Motives are unclear, but I can guarantee they are selfish.

  10. Well don’t mention being a pity date for sure. Just tell him like it is. Ruby set you up with him and you didn’t think it would work out but he changed your mind. That’s the truth and doesn’t insult him at the same time.

  11. Ok, she’s trying to cause a problem, and she’s going to tell the worst possible version of this story. I would let Sean know that his sister seems upset with you and that she was talking about how you met him, and how you originally weren’t sure about going on a date with him when she tried to set you up. But you tried it out, and by the end of the first date you were so into him, and you just wanted to let him know that he should never have any reason to doubt your feelings. Just let him know that’s she’s being weird about it, and that you really liked him as soon as you got to know him at all (in case she tries to make it sound like you were faking your initial connection) without ever using the words “pity date”- at most, it was that you weren’t sure that you would vibe (true!) but you did (also true!)

  12. She set him up out of pity and she’s a terrible sister for wanting to rub it under his nose after all this time. I wouldn’t stand this bullshit. You should tell him what a terrible person Ruby is before she comes forward with her (much worse) version and ruins your chance to get a headstart. At this point it doesn’t really matter what your initial motive was, you didn’t know him and once you did it wasn’t about pity anymore. If I were you I would frame it like yes, you were skeptical due to the physical differences, this might be something that won’t hurt his self esteem and it’s still true. And because you talked to him before his sister chances are he will believe you. Hope you don’t have anything “incriminating” in writing with his sister.

  13. Tell him before she tells him. And explain everything on this post. It will hurt him but just be there for him and tell him about your insecurities too.

  14. Wait wait wait hold up a pity date is very different than settling for someone.

    You can just say, “yeah when I didn’t know you I didn’t think we would gel but I’m so glad I was wrong from the first date I was glad I got to know you, I love you and it was the best decision I’ve ever made.”

    There is nothing wrong with first thinking this might not work before you even know anyone. Just focus on the fact that when you did meet you fell in love. It wasn’t a settling moment it was a dating moment.

    This is very different from the ones you see where it’s “I was dating them but wished I was with someone else but they were good to me.”

  15. i would definetly rephrase this a bit.

    Sure, you can tell m the date was set up by his sister/your friend Ruby. You don’t say you felt bad for him, but instead, you didn’t know him well. All you knew is he didn’t know many people/have many friends and wouldn’t have had the guts to approach him yourself because he came across as big, and a bit scary. But you trust(ed) Ruby, had a good time, the rest is history.

    Also make sure you tell him this because of what Ruby just said, and how she tries to spin the story.

  16. Don’t frame it as a pity date, frame it as somebody would like to set you up on a blind date.

  17. Ruby is manipulative. She thought her brother was lonely, asked for you to date him. Now that you are happy, she wants to rip it all away for him? I hope this isn’t real.

    Edit: if she decides to spin her toxic web, you can tell him she introduced you to him, and you’re so happy she did because you got to meet the best human you’ve ever met and you can’t wait to live your life with him.

  18. I don’t understand why this is something that needs to be brought up at all. It can only cause heir. I’m sure you could frame this in a different light if this Ruby person actually intends on bringing it up.

  19. You don’t have to tell.him you accepted because of pity. She asked you to do it. And you said yes. Case closed. Lots of people have first dates because friends suggest them.

  20. Ruby is a witch!

    Tell Sean that for some crazy reason Ruby came to you and basically threatened you over nothing. That back when Ruby was your best friend she suggested you go out with him because you were the only gay guy she knew that was around his age. You agreed and asked him out and the two of you had an amazing time and the rest is history. Now she came to you and said something about her suggesting that first date and your reaction. You never told him because you never thought of it. Then she said if I didn’t tell you she would.

    I don’t get it. I asked you out, you said yes, we fell in love. What’s the issue? Then see what he says. Ruby is a drama queen who likes to cause trouble. I’m betting she’s not married. She doesn’t want to see her gay brother get married before she does so she’s trying to destroy her. Don’t let her. Never let the word “pity” come out of your mouth. First dates are for learning about the other person. You did and found an amazing man! You tell him that.

  21. Lie.

    She wanted you to pity date him. But you profited the opportunity to approach him since she helped it. You never tell her. She still believes it was her initiative. She would probably sabotage your relationship if you had spilled the bill

  22. Let her tell him and have her try to explain that she is the one who pitied him so she set up the date.

  23. Ruby sucks but hopefully that’s a given. Just don’t phrase it like pity date. “Never really thought about it until your sister put the idea in my head, and I’m so glad I did”.

  24. There’s nothing to tell here, this is how a lot of blind dates are set up. Most people go in with low expectations because they don’t know exactly what they’re getting.

  25. Call her bluff. Don’t tell him.

    It will only tear down his confidence, doing it just before a wedding is especially cruel.

    This person is also clearly trying to stir the pot and cause drama. Best to limit interactions with her in the future.

  26. There is literally no reason to tell him this. What is the benefit? Does it change anything about where you are in the relationship now?

    Ruby actively wants to hurt your fiancés feelings. She’s not a great person.

  27. “I can’t believe we’re getting married. To think I may have never asked you out if Ruby hadn’t suggested it. I didn’t think we had much in common before I got to know you, so I wasn’t sure how we would hit it off but I’m so glad I decided to ask- look where we are now! You’re such a great guy and so sweet and I’m so lucky we went on that date. Let’s play uno!” (Lol at the last line).

  28. You could just say that you want to thank his sister at your wedding, since she hooked the two of you up for your first date and you are forever grateful that it worked out despite you being nervous about it. No need to use the word “pity.” It was a blind date that she set up.

  29. you don’t have to say it was a pity date. you can say that Ruby encouraged you to ask him out – and if she counteracts with saying it was a pity date she looks jealous

  30. Tell her quite bluntly “ there weren’t many gay guys around to date, so there was no pity on either side, I sure as hell got the better end of the bargain”

  31. Tell him during a speech at y’all’s wedding. Heck, even part of your vows. Make it part of your story, make it funny, turn it sweet, end with lots of nice things. If you do it right, he’ll love you even more.

  32. Honestly it sounds less like a pity date than being set up with someone you didn’t know very well. She’s the one that pitied him. That’s a her problem.

  33. He won you over on the first date. Regardless of how it started, it ended well. He likely knows he is shy, and likely knows that others recognized him as being lonely. If he is self aware at all, he will probably laugh it off. Honestly, if I were in his shoes, I wouldn’t care either way, so I don’t know why your friend feels like he needs to know.

  34. SHE pitied him and had you ask him out cause you owed her a favor. She thought so low of him that she cash in a favor for him to get a date. Rephrase it like that for her and ya tell him about it.

  35. i think you just need to be honest with him but like everyone else is saying it’s all about the wording, explain that Ruby set you two up, you weren’t expecting anything to come of it but it ended up being the best thing that ever happened to you because you met the love of your life. i would also add the only reason you’re even bringing it up now is because Ruby is threatening spin an exaggerated version of the story.

  36. WTF is wrong with Ruby?! Since she’s a horrible human being, I suppose you should tell him before she puts a shit spin on it.

    “Ruby asked me to ask you out – and I’m so glad she did; I might have missed meeting the love of life because I didn’t know you well enough at the time to have done it without her prompting. I am the luckiest man alive,” or something along those lines.

  37. Why would his sister do that to him and you? That’s so pointlessly cruel, irrelevant, and not even a big deal.

    If your fiancé trusts you, you can very easily tell him she just set you guys up on a first date and she’s misconstruing it as a pity date. Not to mention the fact you guys are getting married should speak for itself.

Leave a Reply
You May Also Like