Dear Wendy
Dear Wendy

“I Can’t Choose Between My Two Exes!”

For clarity, I’m a lesbian but hate labels. With that said, I’m having trouble choosing between two women, both of whom I’ve dated before. I met ex #1 through work. She came on strong, and we had a very passionate relationship. I don’t think I have ever been that absorbed and given someone that much of myself before. But, after almost a year she decided we needed a break, which I took as an opportunity to meet new people. That’s when I met ex #2. We got together sort of knowing neither of us was in a place to commit to each other and we didn’t have any intentions to. However, we discovered we were really compatible and eventually tried to seriously date, which didn’t work out. Since then, we have stayed in touch and every couple of months we get together.

Currently, ex #2 and I are back “talking” again, but I ran into ex #1 the other day and I just can’t stop thinking about her. She’s gorgeous and truly knows everything about me, though we fought hard though and there are some negative times I really don’t like looking back on. Ex #2 is a bit more practical, very cute and gets along great with my friends and family. She’s loving, thoughtful, caring and totally in to me, so why do I want to risk all that to pursue ex #1? Why do we always go back to the risky ones? Is it curiosity? When I think about ex #1 it hurts because I know I gave everything I had to make that relationship work. I don’t know if I have it in me to ever try like that again. I guess I’m concerned if I’m making the wrong choice… — Between Two Ferns

Generally, the reason we “always go back to the risky ones,” when we have proven troubled history with them isn’t because we’re just so in love or because they have such a strong hold on our hearts or any of that romantic mumbo jumbo we tell ourselves when we’re in the thick of it — it’s because we’re addicted to the drama and not ready for a committed relationship. Think about it: if your exes were like cars and you knew car #1 was a beautiful ride but broke down all the time, then why on earth would you consider purchasing it if what you wanted was something reliable? Clearly, you don’t want reliable. And that’s fine. But quit playing ex #2 who has always been “loving, thoughtful, caring and totally in to you.” She seems ready for something real, and you aren’t there. Let her loose so she can find someone who’s ready for what she has to offer. Go sow your oats with ex #1 — if she even wants you — but be prepared for drama, hurt feelings and probably a broken heart. If you buy a lemon, beautiful as it may be, you have to expect it’s going to break down on you a lot. So, learn how to make repairs when you can, and move on when you can’t.

*If you have a relationship/dating question I can help answer, send me your letters at [email protected].

21 comments… add one
  • ArtsyGirl March 14, 2011, 8:45 am

    Love the analogy!

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  • PFG-SCR March 14, 2011, 8:59 am

    I wish the LW would have shared _her_ current feelings on ex #2, because she only focuses on her feelings for ex #1, and ex #2’s feelings for her. The fact that she didn’t might be a sign that she’s not that interested in ex #2, but it’s a nice, comfortable, “safe” situation with someone who treats her well. While there is nothing wrong with choosing someone like that, she needs to feel some passion for ex #2, or else she’s likely to feel that she’s “settled”. However, it’s unclear what she is looking for – a relationship, casual dating, etc. I think she needs to be introspective about what she wants, and how she truly feels about both exes, and then decide which ex she’d like to pursue something with (based on what she’s looking for). However, it may be the case that neither of them is the “right” fit for her now.

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    • baby.blanka March 14, 2011, 9:51 am

      I had the same thought. I also kind of think that both choices would be the wrong choice as you’ve already tried and did not have a healthy relationship in the past, but sometimes that’s not always the case. I definitely wonder if her attraction to #2 is due to the fact that #2 already expressed interest, so it’s less of a risk to open up.

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  • Beckaleigh March 14, 2011, 9:09 am

    It sounds to me that the LW needs to move on and stop associating with both ex 1 and ex 2. They are both ex-girlfriends for a reason!

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    • Fairhaired Child March 15, 2011, 12:09 am

      I was going to say the exact same thing!

      Also her comment about “Why do we always go back to the risky ones?” doesn’t seem to feel like its only about this current situation described in the letter, but that it’s happened to her before and she recognizes it happening in other relationships around her.

      I believe Wendy, and readers,touched on this with a previous LW about if you broke up, there’s a reason for it, and though you may want to try again after time has passed- that most people try to “forget all the bad” and focus on the “great” times of the old relationships and therefore makes it easier for them to go “Oh I want to date him/her again.. we had such great times .. most of the time” – well its the “other times” that obviously drove one of you in the relationship to breaking point of why it DIDNT WORK.

      I feel like a lot of other comments already posted also feel the same way that the LW should just move on from both and stop dragging things out with ex#2 and even thinking about persuing ex#1. Find someone new who has all the qualities of both of them that you admire so much! Granted you may find some frogs, and you may also surprise yourself, what may be important in your ideal woman now, may not be who you actually fall for later in life.

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  • ReginaRey March 14, 2011, 9:15 am

    I think that whenever we feel we need to “choose” between two people, we’re usually not ready to be in a serious relationship at all…and that’s perfectly OK.

    I was once was in a position where I felt I needed to “choose” between getting back with my ex boyfriend, and moving on to someone new. I chose the new guy, because I was tired of the drama with my ex…and even though I’m glad I did it, it only proved that I wasn’t yet ready for a relationship with ANYONE.

    This may be a generalization, but I think that when you are serious about someone and ready for a committed relationship, you don’t want to be with anyone else or entertain notions of other people. IMO, I wouldn’t try to force it – play the field if you want, but make sure you’re honest about it to both exes (and any other people you may have interest in).

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  • Naneenya March 14, 2011, 9:48 am

    I agree with ReginaRey – if you’re so conflicted in having to choose one or the other, you’re not fully in it with either one.

    I say let exes be exes and go out and find someone that makes the decision easy.

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  • Alletron March 14, 2011, 10:37 am

    I just have to say, I LOVE the LW sign-off on this one. Zach Galifinakis show turned double-entendre? BRAVO.

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      Wendy March 14, 2011, 10:49 am

      I will take credit for that one, thank you. 😉

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  • MellaJade March 14, 2011, 10:55 am


    I would have to advise you to pick neither. The way you described these exes makes #1 sound like a pair of Laboutin heels and #2 sound like a pair of comfy old slippers. While you love and are super passionate about the Laboutins with their hot red soles and 4-inch heels they do hurt your knees, your back and rub blisters onto your feet from time to time. So then you need the comfort, relaxing and nurturing warmth of the old slippers. They don’t appeal to you unless you feel the need to be rejeuvenated. You’re not passionate about them, its all about how good they make you feel.
    I think you need to forego them both, maybe find some sensible pumps to walk around in for awhile or go barefoot until you know what you want.

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    • EatSleepRun March 14, 2011, 11:19 pm

      Love, the analogy, but it makes me sad. In my shoe dreams, really expensive, red soled shoes are comfortable. It’s clearly that I can’t afford really comfortable high heels 😉

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  • Jess March 14, 2011, 10:59 am

    There’s really no evidence that Ex #1 wants to be with the LW anyway, and the ex broke up with her last time… so unless Ex #1 is pursuing you actively and the real question is whether or not to reciprocate, there’s not really a choice that needs to be made…

    by why is the LW trying to pick between these two anyway? just go for option #3 someone new!

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  • HmC March 14, 2011, 11:30 am

    Great advice Wendy, very insightful. If LW were my friend I’d urge her towards option C- BE ALONE FOR CHRISSAKES! If you’re that confused as to whom you should date of multiple options, for whatever reason, you probably shouldn’t be dating any of them. Be single sometimes people, it’s good for you!

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  • JJ March 14, 2011, 12:23 pm

    Last year, I was also in a position to choose between going back to my ex after my seperation or to continue seeing someone new. Even though we hit a rough patch, we were able to work it out and are still together though it is not always perfect. I based my choice on what I wanted and it was not fair to see someone new when my feelings were unresolved.

    LW-I suggest as another reader commented, to take some time for yourself and think about both of your exes and figure out what is important to you right now. There are different reasons why both relationships did not work out and it is up to you to decide what is right for you. I used to be someone in which we would argue every other day practically even though there were some good times. This continued for around 4 years and looking back, I can’t believe that I was with someone who brought me down with his negativity. With ex 1, those same problems and drama that happened then are sure to be brought up again and it will be a continuous cycle. With ex 2, she may be too safe and you enjoy the comfort.

    I think that you should go out and meet someone new that has everything that you are looking for. Whatever you decide, I hope that you find happiness and wish you good luck in your love life.

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    caitie_didn't March 14, 2011, 2:22 pm

    Exes are exes for a reason (or several) and if you can’t decide between two people, you probably shouldn’t be with either of them. When you’re involved with one person, you shouldn’t be having “what if?” thoughts about an ex on a regular basis. I think if you continue this way, you’re really just leading girl #2 on and that’s unfair to her.

    Also, can I rant about people who “don’t like to put labels on things”? I know it’s off topic but for some reason it’s a huge pet peeve of mine when people refuse to “put a label on their relationship”. If it looks like a duck and quacks like a duck, it’s a duck no matter how much you might like to pretend otherwise.

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    • Lexington March 14, 2011, 11:24 pm

      The whole labels thing is such bullshit 🙂

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    Skyblossom March 14, 2011, 5:24 pm

    I think your best option is to skip both ex partners and wait for number 3 to come along. There was to much drama with ex #1 and you don’t seem to have the required feelings for ex #2. Let the past be the past.

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  • Spark March 14, 2011, 6:22 pm

    This is how I read it:

    LW is just not into Ex 2… But she wants to be. She’s trying to convince us, and herself, that Ex 2 is perfect.

    LW wants Ex 1. No doubts there. But Ex 1 doesn’t want LW. She cast her off for a year long break! And LW apparently waited around for a year! And now they just ran into each other. The letter doesn’t mention Ex 1 wanting to rekindle things. If anything, Ex 1 is just looking for some fun. If Ex 1 really, actually wanted LW, they’d be together.

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  • anna728 March 15, 2011, 1:54 am

    Aw I kind of felt sad for Ex #2 on this one.

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    LA March 15, 2011, 8:55 am

    Ex #1 broke up with you. Stay strong and unless she works to get you back, there’s no reason she wouldn’t do the same thing all over again. I was in a similar situation with my current boyfriend and the guy I saw during our break up. When he came back, he had to prove himself worthy and fight to regain my trust. But now it’s been 2 years since then and we’re still going strong.
    Looks like you’re stringing #2 along like I inadvertently did. If you care about her, you’ll let her go so she can move on with her life.

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  • Moe September 20, 2022, 9:04 am

    I am wondering why you broke up with #2. The question to ask is, “What has changed since I dated this person to prevent the struggles we had that lead to the breakup before?” If it is nothing, or just that you are lonely or miss the person, that is not enough. If it is just that she is the person you feel you SHOULD be interested in because she is more stable than #1, that’s not a reason either.

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