AITAH if I go out with the friend of a friend I tried dating once?

Hi Reddit,

Title pretty much sums it up, but context below, I (25M) am going out with a friend’s (30F) friend (30F).

About a year ago, I became a regular at a restaurant in my hometown. From there, I became very good friends with the waitstaff, bartenders, busboys and even owners.

Enter Ally (30F).

We clicked as soon as I met her. Every time I’d see her, we’d talk the entire night and have a great chat. It felt like really good chemistry, so I built up courage to ask her out. She said yes, so we set a date and I took her to a place in the outskirts of town where we had lunch. It was a horrible time. Both of us felt like deer against headlights. There was no chemistry, conversations were very dry, and at one point, she asked a question that just killed the entire vibe. We tried, but it just didn’t work. Water under the bridge. I saw her in the restaurant later that week and it was all good. We sort of came to an unspoken agreement that maybe it’s best if that was kept just where it was. To this day, we’ll talk like if nothing happened and, again, pretty good friends.

Then I met Liz (30F).

A few months ago, I started working temporarily in this new office at my company (I’m a sort of floater employee where they move me to an office where they need me until they don’t and they move me somewhere else. It’s weird, but just trust me on this one). There, I saw Liz. I’ve seen Liz with Ally a few times in town, and even at some events in the restaurant with their mutual friends. When Liz and I started working together, it was only casual and work-related conversations; “good-morning’s”, “do-you-know-what-this-is-about’s”, and “want-some-coffee-I’m-going-on-a-coffee-run’s”. However, the conversations started picking up at some point, and we got to talking a lot more. Eventually, as the floater employee, I got switched to another area where I was needed, but Liz and I kept in touch through text. In fact, we’ve been talking everyday for the last two months. However, I’ve been hesitant to ask her out due to my past with Ally.

But, this last week, she mentioned a restaurant about 2 hours away and said she really wants to go.

As a human from the male species, I’m very oblivious to signals and hints, but even I saw that one.

I suggested we make a road trip, drive up, have lunch, spend the day in the area, and then grab dinner on the way back. She said yes in what was possibly the quickest text message she has replied with.

I really like Liz, but I don’t know if I’m being an AH to Ally. I really feel like the 6-9 months of separation between a date with Ally and the date with Liz is, 1) a long time for things to have settled, and 2) nothing happened between Ally and I.

Am I overthinking? Or AITAH?

6 thoughts on “AITAH if I go out with the friend of a friend I tried dating once?”
  1. UPDATE: Crossposted the original post from another community, latest info below.

    Lotta things happened. Important to note, I was moved by my company to another office once again, so I was no longer working in Liz’s office. However, I would see her in passing every once in a while on company grounds, but I was working in a totally different department so we barely spent any time together.

    Liz and I planned to go on that lunch, but quite literally the day before, she cancelled because of my past history with Ally. She felt that she would be betraying Ally’s friendship by going out with me. I told her I respected that and completely understood, and said we could still be good friends and coworkers. And I thought that was the end of that. Yet it wasn’t.

    A few weeks later, during our office Christmas party, we were all having a bit too much fun and carried the party downtown. There, Liz and I hung out with some of our other coworkers, took some shots, few more drinks, snd got to talking. What did we talk, you might ask? Wish I remembered, but I don’t. Per her words, I had “word vomit, but the good and sweet kind.” 🙂

    A few days passed, and it was all back to normal…Then Friday night came around. I saw Ally and Liz together with their friends out and about while I had dinner and a few drinks, and watched a game. As I was leaving, I received a text from Liz, wondering what I was gonna do and if she could come over after her get-together. I said yes, and waited at my place until she eventually arrived. We started talking, nothing crazy, until she eventually snuggled up with me. One thing led to another, and the rest you can figure out.

    The next morning, we got to talking and we decided that we could give it a shot, see what happened and take it step by step. I was overjoyed…for about 12 hours when she texted me to say she regretted everything and that we should leave things as they were, being friends at best. I’m not gonna lie, that one hurt. She quoted her previous self, saying she didn’t want to compromise her friendship with Ally, and that ultimately she didn’t see a future with me since I was moving out of state in a few months. I, again, told her I understood, and said I would always support her as a friend.

    But then, the most confusing weeks started. She would call/text me at 1 or 2am, asking what I was doing and if she could come by. At this point, I felt emotionally exhausted, and I was starting to feel like a booty call.

    The first two or three times that it happened, I respectfully told her that I rather talk during the day, maybe out for coffee or lunch, but that late at night meetups could lead to events that would only hurt us both. The 4-6 times that it happened after those, I confess I pretended to fall asleep early and would answer in the morning (not so proud of that, but I was genuinely tired).

    After me ignoring her late calls and texts, she sent me a long text saying how she was hurt about me disappearing and how I was playing with her. I responded saying that I’m the one who felt played with, and that I was feeling like a booty call more than a friend or anything. After a few exchanges of texts, I did my best to end things amicably, rather unsuccessfully though.

    So yes, things ended up badly, we barely exchanged glances, hello’s and goodbye’s before I got moved out of state. And for some reason, I feel like the AH.

  2. NTA. But maybe drop by the bar and let Ally know before she starts seeing happy snaps of you and Liz on Instagram.

  3. I don’t get it. You don’t have a “past’ with Ally. Not even remotely. You had ONE DATE where neither of you felt a spark. That is not a “past.” It should not affect any aspect of your life whatsoever… much less who you choose to go out with.

    1. I guess I should’ve provided a bit more historical context, but I’ve been called worse for less before. Like matching with two friends on separate dating apps or having casual friendly conversation with a date’s friend during a double-date.

      Appreciate the feedback though

  4. NTA

    Yes, you are absolutely overthinking this. Your “history” with Ally didn’t end badly, you just realized that you didn’t have chemistry. Further, you didn’t notice this girl because Ally is constantly hanging around you waiting for you to realize you love her. Date this woman. If you feel you have to, text Ally or tell her or whatever, but don’t worry about getting her stamp of approval for dating someone you met.

    Good luck.

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