Dear Wendy
Dear Wendy

“How Can I Let Him Down Easy?”

A few months ago, I met a man online who lives in another city. We emailed back and forth for a few months. We seemed to have a lot in common, including some personal issues we’ve both dealt with. We recently started communicating via phone several times a week. He is a really nice guy and I like having him as a friend, but he’s a little boring, and I don’t feel a romantic connection. Unfortunately, some of the things he’s said have indicated that he may be developing feelings for me. For example, he said that he looks at my picture every day and it gives him pleasant thoughts throughout his workday. I am wondering what I should do to not lead him on. We’re both very sensitive and I don’t want to hurt his feelings, but I’m afraid that whatever decision I make — telling him as best I can that I’m not romantically interested, not returning his calls, or just keep talking to him and hope that he eventually gets the hint — will cause some pain. I know that it would if I were on the other end. What do you and your readers recommend? — Hates the Thought of Hurting Him

If you think you can navigate the rocky roads of romance and avoid pain altogether — either feeling it yourself or causing it for others — you’re being really naive. Getting rejected hurts, and if you’re out there trying to date, there’s a pretty good chance you’re going to get rejected sooner or later. It’s part of the territory, and anyone who’s traversing it should be aware of that. If they aren’t, well, it’s not your fault … unless, of course, you’re the one who’s being unaware, in which case let me try to enlighten you: dating comes with risks and one of those risks includes being rejected. Sometimes that rejection comes right away — a “no” when we ask for a number (or a date); sometimes it comes after a few weeks — or months — of long distance emailing and phone chats; and sometimes it comes after years and years together.

Rejection is never fun, regardless of when it happens, but the sooner it comes, the easier it is to take in the long-run. Rejection after a few months of long distance emailing, for example, will be much easier to handle than, say, after a year of emailing and a request for a visit. Seriously, have you contemplated that yet? What happens when he tells you he has some time off coming up and would it be okay if he came to visit? Are you going to wait until then to tell him you don’t feel a romantic connection with him? I hope not. Tell him now. Be bold about it. Don’t pull the ol’ fade-out (that’s lame), and for the love of god, don’t keep talking to him and hope he “gets the message.” I’m sorry, but talking to someone on the phone several times a week does not send the message that you think he’s boring.

You say you like being this guy’s “friend,” but is that even true? Even though he’s boring? If you do indeed like being his friend, be prepared that he doesn’t feel the same way — especially if you happened to have met on a dating site. People on dating sites aren’t looking for “friends” in other cities they can chit-chat with. And if looking at your photo every day gives this guy “pleasant thoughts,” he most certainly isn’t going to be interested in being “just friends.” What would be the point, really? To be reminded that what he wants doesn’t want him back?

There’s one final part of your letter I want to address and it’s the idea that you like the attention you get from this guy and you’re hesitant to let it go. I guess I’m wondering what else you’d get out of talking with someone several times a week whom you find boring. Maybe there’s some validation for you in knowing this guy in another city has the hots for you. Maybe you’re lonely and you like having someone listen to you. I don’t know. But I’m willing to bet, as much as you hate the idea of hurting this guy, there are some other reasons you’re avoiding “dumping” him, so to speak, and they may be a little more self-serving than you care to admit.

Bottom line: this guy obviously likes you. By continuing to talk to him on the phone several times a week, you are leading him to believe the feeling is mutual. At this point, after a few months of frequent communication, it would be cold to just “fade-out.” Pull up your big girl pants, do the kind thing, and tell him that as much as you’ve enjoyed getting to know him, you’ve recently come to the realization that you simply don’t feel enough of a romantic spark to explore anything more than a friendship with him. It likely won’t be the first time he’s been rejected and it probably won’t be the last, and if he has even a semblance of emotional balance he’s going to be just fine. And so will you.

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

24 comments… add one
  • maynard April 14, 2011, 9:30 am

    I hope this wasn’t online dating and you were emailing for a few months… cause I would avoid that in the future. Just sayin

    Wendy made a lot of great points to think about and I definitely agree with her advice to man up and tell him you’re not romantically interested. She’s right that it’ll be even harder a few more months down the line than it will be now.

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  • Rei April 14, 2011, 9:42 am

    Sometimes, when it comes to the dating world, you just have to hurt someone’s feelings. Otherwise you’d have to date every person who likes you, which would then hurt your other partners’ feelings. Basically, it’s impossible to date without causing a little bit of pain every now and then.

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  • ArtsyGirl April 14, 2011, 9:50 am

    A bunch of emails and phone calls does not a relationship make. LW you have not even meet this guy face to face so freaking out that you are going to break his heart is a little dramatic in my mind. If you really feel that there is nothing romantic between the two of you cut ties and allow him to move on to someone who will be interested in pursuing a relationship. It is not like you are ditching him at the altar, it would be much more cruel if you dragged this out and let him think that the two of you were moving to a relationship.

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  • kerrycontrary April 14, 2011, 9:58 am

    I would follow Wendy’s advice and just bite the bullet. You can’t stay in a relationship with someone (even though I wouldn’t call this a relationship) just to spare their feelings. Both of you will be better off in the long run if you end things now if you aren’t truely interested, because he clearly is. I’m sure you appreciate the attention, but wouldn’t you rather get the attention from someone you liked as well?

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  • HmC April 14, 2011, 10:36 am

    For the love of God, please do not just stop returning his calls, or do that horrible fade out where you call less and less and generally make the other person question your feelings and even their sanity and self worth. As soon as you know for sure that you’re not interested and he is, let him know and be honest. Anyone in the dating game knows they’re taking a risk that they’re feeling may not be reciprocated, him included, so assume that he’s a big boy and he can handle it. Don’t be unnecessarily brutal of course, but tell him you don’t think you guys are quite the right match but that you wish him well. Simple… though of course not easy, I know.

    Just keep in mind that you are doing him a favor, letting him go to find someone who *is* right for him.

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    • HmC April 14, 2011, 10:37 am

      they’re feeling = their feelings

      I hang my head in grammar shame.

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      • sarolabelle April 14, 2011, 10:41 am

        at least you didn’t write in text lingo….

      • Christy April 14, 2011, 10:45 am

        You can edit your last comment, you know! It’s a new feature–I’m pretty sure it’s at the bottom? I’ll edit this one with an update.

        UPDATE: Scroll down to the comment box at the bottom, and next to the Website field, you can “Delete your last comment” or “Modify your last comment.”

        But I appreciate your grammar honesty and shame, lol. (Whoops, text speak)

      • HmC April 14, 2011, 10:53 am

        Hmm people keep telling me about that, but I don’t see that option. 🙁 I guess I’ll have to actually re-read and edit my posts before splattering my fool opinions all over the internet permanently. Boo.

      • sarolabelle April 14, 2011, 10:55 am

        it’s only shows up on your last post. Once you visit another thread and come back to the one you want to edit the option to edit will be gone

      • Avatar photo

        Wendy April 14, 2011, 11:05 am

        It is imperfect, but unfortunately, its the best option I can offer right now. Hopefully, someone will create a plugin that has better editing options in the future.

      • sarolabelle April 14, 2011, 11:47 am

    • moonflowers April 15, 2011, 1:10 am

      Not accidental purple-thumbing again!! So sorry!

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  • sarolabelle April 14, 2011, 10:47 am

    I met this guy online – at first he was so great and we talked and skyped for about a month and then one day we met and you know what, nothing happened. There was nothing there at all – no chemistry. But I kept talking to him because I thought maybe chemistry grows? I don’t know….so I talked to him for about another month. The thing that really kicked it for me is that he was too stuck up on things being his way. Seriously, if I ever disagreed with him it was a big long discussion and he could never see my point. I decided I was going to tell him we weren’t a match. So he called and we talked about the day and then I said “Hey, I think you are a very good person but I don’t think we are a good match.” He accepted it and I didn’t hear from him for about 3 months then he friended me again on Facebook and we talked on the phone once but there was not even a friendship there so about 3 months after that I defriened him on FB and now I never hear from him.

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    • ArtsyGirl April 14, 2011, 10:51 am

      That was the reasonable way to deal with this really common situation.

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    • TheGirl April 14, 2011, 11:17 am

      “I think you are a very good person but I don’t think we are a good match.”

      LW, I think you should use this!

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  • ReginaRey April 14, 2011, 11:18 am

    I totally agree with Wendy…and for the love of GOD, do not do the “fade out.” When people slowly distance themselves from someone, trying to “ease them out” and “hoping they’ll take the hint” the only thing they do is drag out the pain for the other person. It’s happened to all of us, I’m willing to bet – You slowly hear less and less from the person, and because you’ve felt them pulling away you begin to question “What have I done wrong? What’s changed? Maybe if I cling even MORE they’ll start talking to me more again!” In that case, he’s now more insecure than he was originally, and you’re still left with a clingier, MORE eager boring guy who you don’t want a relationship with. Be direct. There should be more people in the world willing to just tell it like it is honestly, albeit kindly.

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    • HmC April 14, 2011, 11:30 am

      Sing it sister. And you know what is the absolute worst of all? When you start questioning whether the other person is even *really* pulling away, because they’re being so subtle, or if maybe you’re being paranoid and hyper sensitive… you think, maybe I just need to be cool, give him space, cuz I’m a cool girl! Then three months later your heart and self esteem have slowly melted into a puddle of confusion and sadness. Be the bad guy up front people! Rip off that band aid! You’re not God’s gift to man (or woman) kind. They’ll find someone new, so set them free!

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  • cmarie April 14, 2011, 11:22 am

    I’m going to defend the LW a bit and say I don’t think it’s about wanting to keep the attention, or validating her hotness. Sometimes you can talk to someone, thinking maybe there’s a spark, or hoping to start one because you have so much in common with another person you know it would be perfect. The way Wendy put it made her sound deliberately cruel; if that were true she wouldn’t even be concerned with letting him down easy, she would just continue to enjoy the attention before the eventual fade-out. Unfortunately, it’s such a common problem in new relationships. I first have to question whether or not SHE is the one reading the signals wrong, maybe he isn’t in to her romantically either and is just interested in being her friend. I have pictures of my close friends and when I look at them they give me pleasant thoughts because they’re my friends and they make me happy, doesn’t mean I want to date them. My advice is to the mature, and kind, thing and just let him know that you value his friendship as just that, friendship. Don’t subtly “friend zone” him either, just come out and say it. Boring as he may be, you obviously have a connection with him and if you want to maintain that, either for the future or just for memory’s sake, you need to be honest.

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  • Rachel April 14, 2011, 1:03 pm

    Wow, I don’t talk to anyone on the phone ‘several times a week’. Definitely tell this poor guy the truth before he becomes attached.

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  • Bethany April 14, 2011, 1:03 pm

    As someone who has been on both sides of this scenario, I have say that I think saying that you’re not really feeling it in the most direct, specific way possible is the best and easiest way to go.

    As an example I had a guy tell me after 3 dates that he didn’t think it would work out between us because I was “too into running and my cat”– He dissed 2 of my passions in life, and I was glad to be rid of someone who didn’t like the core of who I am.
    On the other side, I dated a guy for waaaay too long because I couldn’t make up my mind about if I really liked him or not and we had very different values and wanted different things out of life. I realized this was a crappy thing to do, and I flat out told him, “You and I want different things and I’m not willing to compromise and I don’t want you to compromise” And that was it.

    When you’re direct and to the point, they can’t try to argue or change your mind, and they won’t be left with any lingering questions.

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  • justpeachy April 14, 2011, 3:13 pm

    So are you two in a relationship or are you just friends and he’s hinting that he has feelings for you? I’m sure I’ll get called out on this because it can be kind of shady, but if you are just friends and want to remain that way, you can always start dropping hints (albeit them false) about someone you’re interested in in your town. Odds are he’ll get the message pretty quickly that if you’re interested in someone else, you are not interested in him. That gives him a bit of the power to either try to maintain a purely friendship relationship with you or to fade out of your friendship. Maybe looking at your picture just helps him through the day because he knows he has a friend out there and you shouldn’t kill the friendship just because you aren’t 100% sure of his intentions.

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  • anna728 April 14, 2011, 11:25 pm

    I really, really hope she did not meet him on a dating site. She says she’s worried about leading him on, but if that is how they met, I’m afraid she began leading him on as soon as they started talking. Even if that isn’t how they met, I feel like there are pretty high chances he assumed this was headed in a romantic relationship to start with. If he thought it was originally a just-friends thing but he had only recently developed feelings for her, I think he would test the waters a little more than just saying that he looks at her photo everyday and it brightens his day. No matter what the case, though, she certainly does have to be straight with him.

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  • kali April 16, 2011, 12:13 am

    OK, I know LW says she’s sensitive but am I the only person who thinks that perhaps, just perhaps, they traded photos (we *know* he has a pic of her) and she’s less than enthralled with the poor guy’s appearance? Shallow, yes; but we all know it happens. If that’s the case, she definitely needs to do as others here have suggested: be honest as far as her lack of interest in anything romantic and let him know to look elsewhere. I love the “you’re a good guy, but we’re not a good fit” line. Go with that sentiment — and soon. No sense letting the poor guy continue to smile at her photo and build a future in his head.

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