Dear Wendy
Dear Wendy

“How Can I Stop Comparing Men To My Best Guy Friend?”

I’m 30 years old and I had my first and only boyfriend when I was 19. He and I had a good relationship, but we weren’t in love and I haven’t had a boyfriend since. My excuse is I used my twenties to go to college, work and become as successful as possible. I met a great guy in college who became one of my best friends, but he’s married now. I’m ready to get back into the swing of things and start dating again, but for some reason I compare men to him. He made me laugh, he was incredibly sweet, we were buds…

Over the years, I’ve just met jerk after jerk, just wanting to get into my pants. What am I doing wrong? Am I looking in the wrong places? I’ve tried the whole internet dating several times, and I’ve met one too many creeps, and one went completely wrong — like, his picture didn’t match what he actually looked like and he was much older, like grandpa older. I’m getting older myself and I want to get married and have kids one day. I’d like to start somewhere, but where and how do I go about finding a great guy, without comparing him to my college friend? — Hung Up on an Old Friend


Why is it such a bad thing to compare men to your old college friend? You said he was incredibly sweet and made you laugh, and presumably those are qualities you’d like to find in a mate, no? Furthermore, you and you college bud had a close friendship, which is also a necessary foundation for a strong relationship. In fact, I’d argue that if you’ve been meeting jerk after jerk, you should be trying harder to find guys who are like your old friend. And if the problem is that you don’t know where to find those types of guys, here’s an idea: ask you old friend for suggestions! Or, if you’re no longer in contact and don’t want to reach out to him for help finding a boyfriend, because, let’s face it, that would probably be a weird way to re-connect with an old friend, why not imagine where someone like him would spend his time?

But, I have a feeling I’m over-simplifying things here. Maybe in between the lines of your letter, what you’re really saying is that you were in love with this old friend and you don’t know how to get over him. Maybe you’re even scared that because your love for him was unrequited — one can assume — that you’re doomed to unrequited love forever. Maybe deep down, you’re afraid you don’t deserve a “great guy.” I’m just not sure. What is painfully clear from your letter is that you feel hopeless and a little desperate, and one thing I can assure of is this: you are not hopeless. There really are wonderful, great men out there, and at just 31, you have not lost your chance to meet them. (But if you feel like you don’t deserve them, that’s something else altogether that will certainly stand in your way of a healthy relationship, and I’d recommend therapy to help you address where that feeling comes from and how to get over it.).

As for the where to look for your great guy, I’ll tell you what I tell everyone who asks that question: look everywhere. Keep your eyes open when you’re out and about. Great guys shop where you shop. They go to movies where you go to movies. They hang out at the park on a nice day, and walk their dog around the neighborhood, and drop off packages at the post office. They socialize with the people you socialize with, so say “yes” to more invitations. Go to singles events in your area. Join some clubs or intramural sports teams. Explore hobbies that are of interest to you — especially ones that get you interacting with others. Tell your friends you’re on the market and ask if anyone has someone to set you up with. And don’t be afraid to give online dating another try. Just because you had one bad experience doesn’t mean every experience is going to be bad. It only takes one good one to make a successful match.

Maybe the theme of your letter, if there is one, is not to let one disappointing experience — one unrequited love; one member of the online liar’s club — define you or your search for a relationship. If you keep doing that, you will be old before you know it and still alone. So, let go of the disappointment. Let go of whatever hurt and fear has been holding you back. Renew your search for love with a healthy attitude that there is someone out there for you and as long as you are open to finding him, you will. And while you’re looking, remember to smile, make eye contact and be friendly. Great guys are looking for great women, and the best way to show that you’re one of them is to be open and welcoming. I bet if you talked to your old college friend, he’d give you one more piece of advice: be yourself. It’s the only way to find your right match.

*If you have a relationship/dating question I can help answer, send me your letters at wendy@dearwendy.com.

25 comments… add one
  • avatar

    sarolabelle March 21, 2011, 3:10 pm

    My friend met her guy in the checkout line at Target! They really are everywhere!

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    • avatar

      MissDre March 21, 2011, 10:00 pm

      It’s true. My brother met his wife online. I met my current boyfriend on the same site. I met my ex-boyfriend in a strange way… a friend of mine met a guy online and asked me to come along for support when they met in person for the first time. That dude also brought along a friend to be his wingman… well I ended up in a relationship with the wingman!

      My best friend is married to a guy she knew years and years ago… he was the friend of an ex-boyfriend and she never would have dreamed at the time that she’d be attracted to him. She bumped into him again years later, they ended up married within a year.

      You never know where love lies 🙂 You just have to be positive and receptive!

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  • avatar

    RoyalEagle0408 March 21, 2011, 3:13 pm

    I agree with Wendy about there being nothing wrong with comparing everyone to a really great guy. My best friend is a guy and there are 2 other guys who I’ve known longer that were, and still to an extent are, my litmus test for guys.

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  • eelavocado

    eel avocado March 21, 2011, 3:21 pm

    “They socialize with the people you socialize with, so say “yes” to more invitations.”

    This is great advice that I also received when I was single! In 2008, my then-new roommate was having a little birthday happy hour and also invited her coworkers. It was cold and I wasn’t in the best mood for going out, but I put on some cute clothes and went anyway. It ends up that my now boyfriend was also feeling the same way and forced himself to go as well. You really meet people when you least expect yourself to. If I hadn’t gotten myself out there, I would have never met my great guy. Good luck!

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  • avatar

    ReginaRey March 21, 2011, 3:23 pm

    Such excellent advice, Wendy. I very much second your third paragraph – you are SO much more likely to meet someone when you’re out there doing things you enjoy, and when you open yourself up to socializing a bit more.

    I’d also add – don’t view dating and men like you’re trying to fill a quota…I’ve seen a lot of women dating guy after guy after guy, thinking the more guys they have coffee with the more likely they are to find love. But there’s something to be said for having select meaningful interactions…perhaps the key is quality, rather than quantity – get very good at knowing what you want in a potential mate, within reason, and don’t settle for trying to force things with guys you meet online or go on a few dates with. If he isn’t what you want, then move on. The great thing is, as Wendy pointed out, you DO seem to have a guy who you can compare and guage against. I would use that to your advantage…but remember that sometimes you may *think* you know what’s right for you, and you end up being completely wrong. If a man is different than your friend, yet still appealing in other ways, don’t write him off…there is no carbon copy of your friend, but that doesn’t mean he can’t be better.

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  • avatar

    ArtsyGirly March 21, 2011, 3:37 pm

    If you still are having bad luck I am going to suggest something a little extreme – nowadays there is a growing number of match makers, think of it as a more specialized (and yes more expensive) form of online dating sites. If you go for it you can sit down with a match maker and vocalize exactly what you are looking for in a partner and they can help direct you to people and even in some cases they will direct you to activities which will help you meet the right guy,

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  • avatar

    Theenemyofmyenemyisagrilledcheesesandwich March 21, 2011, 3:50 pm

    I agree with most of Wendy’s advice, but I’m still a little worried by how much the LW is comparing potential mates to the friend. Especially if she isn’t in contact with the friend anymore, I would suspect some idealization of the person and the relationship, which certainly isn’t going to do anyone any favors. (No one wants to walk into a relationship with the pressure to live up to someone else.) It’s wonderful to have a well constructed idea of the qualities you want in a mate( i.e., kindness, humor, the ability to be intimate), but these probably need to be abstracted so that the LW is able to see them generally in people, not specifically like they exist in the friend.

    Based on the other explanations, I’d guess that holding up the friend as an ideal is a way of keeping real potential partners at a distance that they cannot cause pain. Real intimacy is to be actively vulnerable.

    So I think Wendy’s advice on where to meet a great guy is perfect, as usual. Whether or not the LW compares them to the old friend has less to do with the guys than with her perspective.

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    • avatar

      justpeachy March 23, 2011, 4:18 pm

      Ok, random tangent, but I LOVE your name!

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  • avatar

    rainbow March 21, 2011, 4:06 pm

    I have a feeling that what LW really wanted from Wendy was encouragement to go declare her love to the married friend. The whole letter reminded me of a rom-com “how can she not see they’re meant for eachother!” situation kinda staged.
    I’m not saying she did it on purpose or was trying to trick anybody, but it seems to me that under all the questions what she was really asking for was permission to have hope.
    Anyway, I hope she meets someone cool to make up for all the weirdos. The only advice I could give her about online dating is that if you read someone’s profile and they sound deep and slightly tortured, though interesting, they’re probably insane. Sane people try to sound fun and easy-going, and don’t give off the “i could totally be a dead poet” vibe.

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  • avatar

    sweetleaf March 21, 2011, 4:17 pm

    I identified with this letter so much and I think Wendy was right in saying that the LW doesn’t believe she deserves a good man. I’ve always struggled with not believing. And like the LW, I compare all potential suitors to “the one that got away”.

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  • Heather

    Heather March 21, 2011, 4:50 pm

    My immediate reaction is that the LW SEEMS to still have feelings for her old flame…that’s just the feeling I got. I agree with all of Wendy’s advice on how to meet guys, etc. And I don’t think there’s anything wrong with comparing guys you date to the positives about previous relationships. Isn’t that what they’re for? To seek out the good and avoid the bad as much as possible?

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  • avatar

    SpyGlassez March 21, 2011, 5:56 pm

    1) I met my bf through a community college course.

    2) Don’t think of each date in terms of “MARRIAGE! KIDS! NOW!” because guys can smell desperation, and it smells like a zombie saying, “BRAAAAIIIIINNNSS!”

    I agree with what Wendy said; it does sound like the LW is perhaps trying to recapture a halcyon college experience and friendship, that either unrequited love has lingered OR that she’s raised this friend to sainted status.

    Either way, the best thing I can offer is this: I met my BF at 28, when I had given up “looking” and was enjoying “living.” So stop the manhunt and enjoy your life!

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    • avatar

      MissDre March 21, 2011, 10:03 pm

      Don’t think of each date in terms of “MARRIAGE! KIDS! NOW!” because guys can smell desperation, and it smells like a zombie saying, “BRAAAAIIIIINNNSS!”

      ROFL this gets my vote for quotes of the week, I laughed out loud!!

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  • caitie_didnt

    caitie_didn't March 21, 2011, 6:15 pm

    I definitely agree; I think the LW still has feelings for her long-time friend. Here’s the thing though, many people have “the one that got away” or that one ex where the relationship was great until it ended, who you think about with “what if we hadn’t been so young and immature?” or ” what if i hadn’t have moved for school/work?” or whatever. You have to try really hard to put that person behind you so you are available to meet new people (i also believe that there is something to be said for letting the universe know you are ready for something). I think the LW may be almost unconsciously sabotaging herself because she believes there isn’t anyone out there who is as good as her friend. So she picks the guys she’s least compatible with to reinforce that, and is getting more and more frustrated.

    I’ve been having a crappy few months academically and personally and my mom keeps telling me “things will work out for the best”. I’m not sure how much I believe that, but it’s still nice to hear. Maybe the LW needs to start thinking in terms of this- that her and her friend were not meant to be more than friends and there is someone else out there for her.

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    • avatar

      Woman of Words March 22, 2011, 12:36 am

      …Even that there is someone BETTER out there for her!
      LW, try not to become despondant. A great attitude (albeit under frustrating circumstances) will be an ideal asset when hoping to meet someone. Good luck!

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  • avatar

    Elle March 21, 2011, 6:24 pm

    Wow, LW, let it go already!!! I used to like a guy in high-school, I couldn’t stop thinking about him all the way through college. But I got over him. You need to get over your buddy too. Albeit, you’re about a decade late.

    I find it hard to believe you haven’t met any decent guys since you finished college. You must have, but you were emotionally unavailable to them. (Google “Emotionally Unavailable” – it will be an eye-opener). Maybe you weren’t attracted to the decent guys you met, and that’s ok. But I find it hard to believe you met a string of jerks only. (I did meet a nice guy online. I wasn’t that attracted to him, and that’s why I decided to stop seeing him (he was also a bit desperate…). But he is a nice guy! They all come in different packages, you know?)

    Open yourself to the possibility of dating a guy who’s not like your buddy. You might be surprised. You just need to change your mindset.

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  • avatar

    ele4phant March 21, 2011, 6:33 pm

    Great advice, but I wonder if its not that she’s in love with him, but that her close friendship with this guy may block her from finding someone as he is currently fufilling all of the emotional needs a boyfriend provides. She didn’t say whether or not they are still close, but if they are it might be a factor.

    When I was in college, I had a really, really close guy friend. I too was only finding guys that wanted to sleep with me but nothing more. At first I attributed this to the fact that we were all in our early twenties, but eventually I realized that my friend was filling the role of boyfriend (excluding the physical stuff).

    If they are still really tight, maybe scaling back the amount she relies on this guy emotionally might make room for someone else.

    Just a thought.

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  • avatar

    spot March 21, 2011, 6:47 pm

    “Over the years, I’ve just met jerk after jerk, just wanting to get into my pants.”

    Do you think part of what made you think so highly of your best friend was that he appreciated you purely for your character, and nothing physical?

    When you say they just want to get in your pants, do you mean they really wanted you for nothing else except sex *or* that they were clearly interested in you sexually? Sexual attraction is crucial in finding a mate and I would be worried if a guy I was dating wasn’t trying (mind you, subtly and respectfully) to become intimate with me. There is something to be said for taking your time, and if those guys you went out with were not comfortable at your pace, that is one thing, and they indeed are jerks, but did you give them a chance by setting a clear pace or did they have to guess what you wanted?

    I don’t know your situation and yes, there are lots of jerks out there who are only interested in sex at the moment, but try not to write off every guy simply because there are interested in sex. Be flattered that they find you attractive, set a *clear* pace for the relationship, and give them a chance to go from there.

    Best of luck to you!

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  • avatar

    AKchic March 21, 2011, 6:57 pm

    *shrug* My best friends are guys. I’ve even adopted one as a “little brother” (he’s younger than me by two years, but a foot taller than me). Surprisingly, I met my current guy (4 years strong, with one son together) at a bar, when I was hanging out with a few friends after I’d gotten back from spreading my grandpa’s ashes with family.
    It’s not bad to compare potential suitors to your friend and former boyfriend. Just make sure you aren’t putting him on an unattainable pedestal. Ask your guy friend and his wife to help you out. I’m sure they would. Maybe he has a brother or cousin that might spark your interest. Maybe she has a brother/cousin/friend like your friend. You won’t know until you ASK.

    Good luck.

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  • Jess

    jess of citygirlsworld.com March 21, 2011, 9:22 pm

    I met my boyfriend through my brother-in-law because he thought we’d be a good match. But it was a one-way match and my future BF had no idea that it was a set-up. We talked but he never made a move so I figured he wasn’t interested. Months later, we both joined Ok Cupid where he was confident enough to reach out. Finally we had our first date and the rest is history. If I hadn’t been looking for love on multiple fronts, we wouldn’t have come together.

    Point is that, like Wendy said, you have to keep ALL of your options open. Think of dating as a part-time job. It’s not your main focus because you have a full and active life outside of it. But it’s not something you can blow off either. Give it no more or less importance in your life, and you’ll be headed in the right direction.

    He’s out there!

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  • avatar

    Jem March 21, 2011, 10:03 pm

    I’m not going to speculate about whether or not you have unresolved feelings for this friend; I don’t have enough information to tell. I am going to suggest you look closely at your relationship with him. What are the one or two things you liked most about him? Those traits might give you a clue about who you’re really looking for.

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  • fast eddie

    fast eddie March 21, 2011, 11:27 pm

    If I had “the answer” to this age old question and sold it retail the bank wouldn’t be big enough to hold all the money. I didn’t get lucky until I was committed to finding someone and making it work no matter what if took. That word lucky is truly what it was and remains to be so.

    I went cruising on my sailboat and being alone for days at a time with no one to talk to that was my independence Waterloo. After 3 days at sea the seagulls start talking to you. On the 4th day you answer them. On my return I encountered an old friend who had given up finding a guy and rest is the stuff of legend.

    Back to her problem: Don’t worry too much, at 30 you have enough time and seem intelligent enough not to settle for Mr. Wrong. It wouldn’t hurt to let your guard down a bit, be open to any and all opportunities.

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  • avatar

    Caroline March 22, 2011, 1:44 am

    Wendy, your advice on finding a guy is so spot-on! I met my current boyfriend through a really good mutual friend of ours. Actually, it’s funny because I first saw him at our friend’s Christmas party in 2009 but didn’t get a chance to try and talk to him and didn’t think he had even noticed me. So I didn’t really think anything of it, plus I was still pining after another guy (ugh, I wasted two and a half years of my life pining over him). Well, fast-forward a month later and I get a text from my friend saying that the guy had thought I was cute too (she had been talking to him about the party and mentioned that I thought he was cute, and he asked if it had been me since he thought I was cute also) and he added me on Facebook later that day.

    It could have not gone anywhere. After all, to start out on Facebook – well, I’m not saying that people who meet on Facebook won’t have a good chance, but really, meeting in person is so much better – I wasn’t sure what to do next, if I should start talking to him a lot or wait for him to start talking to me a lot or what. Anyways, a day after that it ended up being his birthday and our friend told me to come to the surprise party that she and her roommates were having for him. I was reluctant at first since it was his birthday and I hadn’t even met him in person! But I made myself go, got out of my comfort zone, and I am really glad I did. We’ve been dating for over a year now and are still going strong. 🙂

    But I think, also, you have to let yourself be open to the possibility of love. I ran away from a lot of guys because I was so hurt by this guy that I had been pining for. To me, he seemed to be so perfect and I didn’t understand why he didn’t feel the same way about me. I didn’t think I would find someone I liked as much as I had liked/loved him. But I was proven wrong, and I actually ended up with someone that I never expected to fall for. So, who knows? LW, you just have to take a chance. What do you have to lose, anyways?

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  • avatar

    Wendy March 22, 2011, 8:47 am

    I met my husband at a church retreat. My sister invited me along (I didn’t belong to her church). My husband was invited by his neighbor. He didn’t belong to that church either. Like Wendy says, good men are everywhere, even at the most unlikely places.

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  • avatar

    justpeachy March 23, 2011, 4:21 pm

    My advice would be to take a night class at your local university or community college, preferably on the graduate level. These classes are full of people who work all day (so you at least know he has a job) and full of people who are closer to your own age. Also, you’ll have 4-12 weeks to talk to any potential guys, build up a slow flirtation, and at least find out if they are jerks before things go too far.

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