Dear Wendy
Dear Wendy

Updates: “Hopefully not 40-Year Old Virgin” Responds

It’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing today. After the jump, we hear from “Hopefully not 40-Year Old Virgin,” the 26-year-old self-described “nice guy” who had never kissed a girl. He had been dipping his toes into the online dating pool with only lukewarm reception. We all told him to change his attitude — and his profile! — STAT. Keep reading to see how he’s faring now.

So it’s been a while, and figured it was time for an update.

First off: Wow. I’ve always prided myself on being able to understand where others are coming from, and to put myself in their shoes, and to give them good advice. When I read your response, it was like a splash of cold water. Scratch that, it was like the heavens opened up and friggin Niagra Falls came pouring out directly onto me. Thank you.

I read, and re-read, your letter and the responses from readers many, many times as I rewrote my profile on match. I took out the negativity and put in the quirkiness and boyish-yet-wise-beyond-his-years lens from which I view the world. And it worked! I met a woman who, after our second “date” (not counting the first meeting over a drink after work) I walked to her front door. She turned to me and said “Ok, NOW you stop being shy.” I had no choice but to go in for the kiss. Straight outta a movie, I know. Then after another date (where we kissed again)….she quite abruptly ended things. I still don’t get what happened; I guess you could say I got mind-fucked.

Ah well, C’est la vie. I’m keeping my profile alive, tweaking it now and then to incorporate what little I’ve learned from my limited dating experiences, but overall keeping that same positive outlook.

“I think I can, I think I can” said the little train.


I don’t know — I wouldn’t necessarily say you were mind-fucked. Dating is about getting to know people and seeing whether you match up in the long run. You can’t figure that out on a first date (I mean, not usually), so I don’t see how one could “abruptly” end things after a third date. End what? Three dates doesn’t really make a relationship. At any rate, keep on truckin’. It’s a numbers game — the more dates you have, the more experience you get and the better your odds of meeting Ms. Right. Good luck.

If you’re someone I’ve given advice to in the past, I’d love to hear from you, too. Email me at wendy@dearwendy.com with a link to the original post, and let me know whether you followed the advice and how you’re doing now.

23 comments… add one
  • avatar

    Christy February 27, 2012, 1:14 pm

    It’s all about being able to day to yourself “Look, I’ve done this once. I can do it again. It will never be as awkward as the first time.” Seriously, yo. You’re past the hardest part.

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  • Will.i.am

    Will.i.am February 27, 2012, 1:15 pm

    You are doing the right thing. Just try and keep your head up. One word of advice, don’t go on a date with a girl you really aren’t that attracted too. I’ve did it once or twice and it was the biggest mistake I’ve made with online dating. I tried to give them the benefit of the doubt and really put a lot of thought into the personalities. Sadly, they both lacked in that category as well, so then I was really disappointed.

    Online dating is an easy way to get discouraged, since it’s viewed as an “option” and many people think there better match will log on or join the next day. It’s sad that it’s that way, but when you truly have those many “options” you can tend to keep waiting for a match that will never come.

    Something else I read that I liked, was to kill your profile for a while, if you have been going on dates for a couple months with no success. I’m about to idle my account for a couple months, so when and if I have to come back, I won’t have a stale profile.

    Just play around with it and always try and have fun. The moment you find it to no longer be fun, take a break from it. Dating should still be fun, even if the outcome isn’t to your liking.

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    • sobriquet

      sobriquet February 27, 2012, 1:57 pm

      I disagree slightly. If you like their personality, give it a shot. Where’s the harm in that? Now, if you’re not attracted to them after the first date, don’t pursue it anymore, but you never know what will happen. I wasn’t attracted to my boyfriend via his Facebook photos, but we had a good time chatting, so I decided to meet up with him for a drink. After spending some time with him in person, I was extremely attracted to him. We just had a chemical connection, I guess. We’ve been together for 3 years.

      Pictures don’t always accurately portray how attractive someone is in real life.

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      • avatar

        2_J February 27, 2012, 2:08 pm

        Sorry to stray a bit from the LW, but i’m going to go out on a limb here and suggest that Will.i.am possibly , like myslef, had seen a few photos of a few women on their profile, maybe they were angeled , maybe not, whatever the case, he was probably attracted to them from the start, however, he did say he met them in real life, as you say. Boy oh boy how hard it can be once you meet the person and the photo looks almost nothing like them, blame it on how old the pic is, lighting….whatever, but i can see how this is very frustrating, especially when they have good personalities but if the physical attraction isn’t there…

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      • Will.i.am

        Will.i.am February 27, 2012, 2:58 pm

        I have a mixed bag on this one. If I meet a woman in public while somewhere and I’m not initially super attracted, but I dig her personality. I just can’t get that from an online dating profile. My personality doesn’t come out typing and well as it comes out verbally.

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      • Budj

        Budj February 27, 2012, 3:37 pm

        I type with so many … because it is kind of how I talk… I’m weird… it also separates phrases and or sentences… yes… It’s also a weird habit of having to still be pressing a key while I think of what to say next… it also results in a lot of run ons.

        Believe it or not I actually earned A’s in all of my college writing classes.

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    • iwannatalktosampson

      iwannatalktosampson February 27, 2012, 2:02 pm

      I just want to repeat everything will.i.am said. Don’t get discouraged, she just wasn’t the right one. But I’m glad you got that first experience out of the way and hopefully you can remain confident in the future! Good luck!

      P.S. lots of girls like shy guys. I married one, it’s amazing.

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      • avatar

        Addie Pray February 27, 2012, 2:16 pm

        GOOD LUCK TOMORROW!!!!!!!!!!!!!!!!!!!!!!!

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      • avatar

        MissDre February 27, 2012, 2:33 pm

        What’s tomorrow??

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      • avatar

        Addie Pray February 27, 2012, 2:36 pm

        She and HmC (and other?) are taking the bar. They’re probably shitting in their pants right now. I think I was about this time.

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      • iwannatalktosampson

        Iwannatalktosampson February 27, 2012, 2:53 pm

        Actually I’m not. I am just so excited to be done with it that I have no room left for nerves. I have my outfit for tomorrow layed out, all my stuff I need to bring set aside (my red bull packed, my Xanax in my little zip lock baggy) – I am ready to go. Plus I have all fun activities planned for the rest of the day so I get my mind off it – I’m on my way to a facial – then going to yoga – then taking my puppy to the dog park – then watching some Teen Mom tonight!

        But thanks! Pass of Fail – Wednesday is a victory because I won’t have to look at this shit for at least 3 months!

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      • avatar

        MissDre February 27, 2012, 3:26 pm

        I’m sort of ignorant and don’t know what’s involved in that but…. GOOD LUCK!

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    • avatar

      Addie Pray February 27, 2012, 2:18 pm

      I agree with Will.i.am. And hey she kissed you again, which means your first kiss couldn’t have been that bad, congrats! It will get better and better from here on out. She was your practice round. The next girl will be a better fit. Or not. But it’s sure fun to give it a try, eh?

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  • AKchic_

    AKchic_ February 27, 2012, 2:18 pm

    I’m going to tell you something – I hated online dating. The “guys” I met there, I could have met elsewhere. In fact, two of the guys I met online, I KNEW from mIRC. Anchorage is truly a small world. One guy I “met”, I worked with previously, and once I “met” him, I realized that he’d lied completely on his profile.
    None of the guys I’d met online clicked with me.

    Some people – it works. Some people – it doesn’t.

    Don’t get discouraged yet. Being in the “lower 48”, you have a bigger dating pool than up where I am. Your odds are better (and the “goods” aren’t as odd!). Being a late bloomer isn’t a negative. It means that a woman doesn’t have to worry about STDs if she chooses you. She can mold you into her version of the perfect sexual partner.

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  • Will.i.am

    Will.i.am February 27, 2012, 2:39 pm

    Even though it didn’t work out, like Addie Pray said, you did get a kiss twice. It’s much better than getting a hug or a handshake. Sometimes you click, but she clicks more with someone else. Or maybe she’s more interested in a guy that isn’t all that interested in her.

    It’s a numbers game and you never know till it’s the right one, if you are number 1 in her life or number 10.

    AkChic: I have the same reservations you have with online dating, but I do keep trying. I’ve had some good dates, but I’ve had more bad then good. I’ve learned a lot about myself and truly what I’m looking for. That is what online dating has showed me. I know 100% what I’m looking for and what I want out of a partner.

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  • kmtthat

    kmentothat February 27, 2012, 2:51 pm

    Online dating, ahh the joys. I will say that in addition to putting yourself out there, when things don’t work out with someone, be sure to end it classy. I don’t know how many of my friends think it’s ok to just “ghost” on a person hoping that their lack of responsiveness is a perfectly acceptable way of letting someone they met online know they are no longer interested because meh, it’s only online dating. (I think it’s like the madness of people who write horrifically in text messages/email…they kind of don’t take it as seriously as “real” writing.) Or they take it super harsly when someone lets them know they aren’t interested…don’t be the bitter guy that got rejected; be magnanimous!

    Point in case: I went on two dates with a guy and thought he was a really awesome, sweet person but I didn’t feel romantic chemistry. I let him know and opened it up to stay friends, and he was super gracious about it and kept it classy. I had thought he might hit it off with a close friend of mine, but before I had the chance to introduce them, they met online as well. Even though there were some awkward moments when it all came out, it really wasn’t that weird since I had nothing but great things to say about him. Long story short, they’ve been dating for months and are really happy. If he had been a jerk when things didn’t work out with me, there’s no way my friend would have dated him. Take online dating as a way to meet people, and if it doesn’t work out with them, they might know people that it would work out with 🙂

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  • avatar

    6napkinburger February 27, 2012, 2:59 pm

    So this is quite apropos of my day today: I joined OK cupid today. I am on a different site as well, but i decided that site didn’t cast a wide enough net.

    Let me tell you, I am looking for a nice guy. But nice guy doesn’t mean the same thing as “doesn’t know how to dress, shower, shave, get haircuts, spell, joke, or edit.” All of those things are noticeable and they are some of the only things you have to judge someone’s profile by. Every girl I know looking to find “the one”online wants a nice guy who will love her who she can love, and who they genuinely like spending time together. They just don’t think that it has to be synonymous with “wimpy guy with an inferiority complex.”

    If they have shirtless pics and list working out as their first interest, or “takes care of herself and works out” as their first requirement in what they are interested in, I pass. If their pics are all posed glamour shots, I pass. I pretty much pass on anyone who uses the word “drama” in their profile (as in “I’m very laid back and chill and love life – not looking for a lot of drama and or game playing”), not because I like “drama” but because it demonstrates a lack of maturity in the writer (um no-one wants drama with their future spouse) and a cavalier attitude towards real relationships (that take work) that I’m not interested in.

    But there are a bunch of guys who probably think of themselves as “nice guys” who aren’t getting attention because they are all over the place in their pictures and profile. Some guys come on too strong in their profile with how much they want to find their “soulmate,” which, even if that’s what you want too, comes off as intense. And when they message you to ask you what you want in a relationship in the first conversation, where they want you to list the criteria that you want in a partner instead of chatting with you and having it come up organically … its just too much. So don’t do that.

    Some guys have 4 pics that all look like different people and I hav eno way of knowing who the real person is. So don’t do that.

    And you’re way better off if you never mention “the bar scene” and how much “you’re over it.” Also, friends and family are the most important things in the world to you? Show, not tell people.

    The profiles of the guys that I like usually are a little bit funny, a little self-deprecating while confident and describes a person I’d want to hang out with. They usually mention one “job interview weakness” which is either endearing (e.g. can’t sing well but does it anyway), unimportant but random (e.g. can’t rollerblade ) or isn’t a weakness, so is tongue in cheek as a weakness (e.g. “a penchant for making chocolate souffles without notice but with vanilla ice cream. “)

    Just a few thoughts from someone who spends their nonbusy days reading tons of these and judging them quite harshly.

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    • Will.i.am

      Will.i.am February 27, 2012, 3:12 pm

      It’s funny how many profiles you see that mention, soulmate, hook ups, love of my life, children are my world (I hate this one), and my heart has been broken and I’m tired of getting walked on.

      My profile is pretty generic, since I really don’t put much weight into it. I list just enough to get you intrigued, but I don’t want anyone to read my life story. I also do think I mention that I’m laid back, but I never mention drama.

      I’m on okcupid as well. I seem to get a better response there than the other site I used.

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    • Summertime

      Summertime February 27, 2012, 3:35 pm

      napkinburger – All the advice to this guy has been great, but your comment really lays it out for him in a way I think he needs. Well done!

      LW: This commenter has identified a ton of common pitfalls so, oddly enough, the closer you stay to her suggestions, the more real and like-yourself you’ll be. Online dating is weird because sometimes it feels like there’s this pressure to advertise yourself as a list of dating positives, for someone out there with a checklist.

      But remember: just like a resume is supposed to get you the interview, not the job – your profile is trying to open a CONVERSATION, not land a relationship. And then, the best relationships will flow from the good, natural conversations you can have with someone- my BF and I ran into each other at a frozen yogurt shop, of all places; my mother landed an excellent job after she spent literally the entire interview talking with the interviewer (the big boss – who became her mentor) about pizza! Pizza! Just relax and keep an eye out for the woman you can easily talk about _____ with; that will be the thread that’s fun and fulfilling to pursue. (Do not fill the ____ with relationship stuff.)

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    • avatar

      DramaQueen224 February 28, 2012, 5:18 pm

      Seriously about the “no drama” line, ugh. I also HATE it when the guy says something about wanting a woman who’s not “crazy”. I take it to mean that he’s a jerk who can’t possibly handle emotions other than happy and horny and promptly hit ignore.

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  • avatar

    Marta February 27, 2012, 4:55 pm

    I think he likes to be mind fucked, now he has a ‘war story’ for the guys.

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  • avatar

    wendyblueeyes February 28, 2012, 8:58 am

    Keep on keeping on. On our third date, I just grabbed my husband and planted one on him. He jerked away after about 30 seconds. He was blue in the face since he didn’t know you could breathe during a kiss. We laugh about it still, after 40 years together. He became less shy as time went on. You will too, the more you date, the easier it gets.

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  • avatar

    Leslie February 28, 2012, 6:17 pm

    Way to go “Virgin”! You’re definitely on the right track. Wendy isn’t lying when she says it’s a numbers game. I probably kissed 100 (literally) frogs before I met my prince. The more dates you go on, the better.

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