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“I’m 32 and Have Never Kissed a Girl”

I’m 32 and have never had a girlfriend. I’m not a touchy-feely person, and this coupled with being really shy around women who I’m interested in, isn’t making my life easy. I’ve only been on about four dates since high school, and none of them worked out. I feel all I need is practice, but I get so nervous on a date, that rather than confronting my fears, I’ve been avoiding them. Even something as simple as kissing is foreign and scary for me, as I’ve never kissed a girl. The guy is supposed to take the lead, but this guy hasn’t got a clue!

I was a big teenager, so I never had great self-image and lack confidence. I lost a fair bit of weight, but being big has left it marks both on my skin and on my confidence. My family also moved often so I never had any lasting friendships and the lack of friends has followed me into my adult life. I’ve always felt like the odd one out, and as each year passes it seems to further diminish any romantic confidence. I know I’ve got love in me and much to share, but I don’t know how to find someone to share it with. — 32 Year-Old Virgin


First of all, you need to know that you are not alone in feeling the way you do. I get countless letters from people of all ages — yes, even older than you — who have never dated, don’t know how to date, and feel insecure about their lack of relationship experience. What you need to keep in mind is that there are women out there who are just as anxious about finding you as you are about finding them. So, how do you find each other? Well, casting a wide net is a helpful start. In your search for love, don’t rule out women who are older or younger than you, or don’t look like a movie star. Look for someone you can connect with on an emotional and intellectual level first before exploring how well you connect on a physical level. And treat women the way you’d like to be treated — with respect, sensitivity, kindness, and understanding.

As for where to look for these ladies, online dating was made for someone like you. You get to make your first move from the comfort and security of your own home! You can take your time forming thoughtful questions and responses in your emails, and you’ve got a wide array of women to choose from. Since you were once heavy and say the weight left it marks both physically and emotionally, I’d suggest you check out some dating sites specifically for heavy-set people (BBWCupid.com and OverweightDate.com are good ones). Even if you aren’t overweight anymore, you may find comfort in meeting people who appreciate the struggle you’ve experienced with your weight and the effects it’s had on your self-esteem. You might even be able to inspire others with your story of weight loss, which could serve as a real confidence booster for you.

Once you’ve had enough email — and perhaps phone — interaction with a woman (about three emails each should suffice), ask her out for coffee or a bite to eat. Don’t get so comfortable in your online exchanges that you avoid meeting up in person. From there, you’ll be able to tell whether you have enough chemistry to give a second date a shot — and even if you don’t, perhaps you like each other enough to be friends, which is something you could use more of, right? When it comes time to make a move, don’t over-think it. Be confident! You didn’t know how to walk the first time you took a step, right? You didn’t know how to drive the first time you sat behind the wheel of a car. You didn’t know how to ride a bike the first time you pedaled down the sidewalk. But, sure as shit, you probably do all those things with aplomb now. Kissing — and everything else — is the same way. You’ll figure it out. And if you’ve got a good and caring teacher to show you the ropes, you’ll have fun learning.

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

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{ 20 comments… add one }

  • avatar ReginaRey March 15, 2011, 3:19 pm

    Wendy’s advice is spot-on. I’d also suggest a no-pressure organization for singles. There are usually tons, depending on what area you live in, and they take the pressure out of planning for you. You can sign up for any number of activities, and mix and mingle with people there…it would be a great way to perfect your conversation skills, your body language, charm, etc. The same goes for getting out there and doing other activities that you have an interest in – you’re much more likely to meet someone with shared interests and goals if you’re doing something you already enjoy!

    Also, it’s easy to say and tough to do – but try your best not to get disappointed if you get rejected outright or if it goes nowhere with a woman who you’ve been out on a few dates with. We all struggle to find someone right for us, 32-year-old virgin or not, and it takes wading through a LOT of wrong people sometimes to find the right person. Don’t get discouraged…when you HAVE found someone special, it will be easy and natural, and she’ll appreciate you for who you are…inexperienced kisser and all, I promise!

    You also don’t need to feel awkward or self-conscious because you are inexperienced…there’s no reason to tell women about that up front. That’s something you can choose to share when the time is right. Have a confident attitude, even if you’re faking it for a while…there’s no harm in that.

  • avatar Beckaleigh March 15, 2011, 3:36 pm

    Wendy and ReginaRey have made excellent points. The only thing I would add is that you shouldn’t feel pressured into making the first move! There are plenty of women out there who like to take the lead on such things! And, WHEN you find your someone, everything else will come natural so don’t let it get you nervous!

  • avatar WatersEdge March 15, 2011, 3:39 pm

    I’d like to second that point about how common rejection is in dating for everyone. I was considered to be successful with the gentlemen, but I probably had about a 30% success rate between liking a guy and getting him to spend any time with me… and out of that, maybe 1 in 10 dates lead to an exclusive relationship. Rejection is a standard part of dating, so don’t take it personally. It really is just a numbers game.

    • avatar HmC March 15, 2011, 5:06 pm

      Totally agree, learning to not take rejection too personally is so important to maintaining the positive attitude you really need to attract anyone of quality.

      LW you seem like a sensitive person, and from one sensitive person to another, the best dating advice I can give you is to take things slowly, share yourself gradually, and let people earn your trust. I’m not saying to distrust people from the get-go or to think negatively, but please keep in mind that people are on their best behavior during the initial courting stages. So, be happy when you meet someone with traits you are looking for, but give new connections time to breath and don’t lose your heart to someone before they have earned it through their actions over time. If I could go back and tell a young HmC anything, it would be that.

      Good luck to you LW! Your story really tugged at my heart strings. There are many crappy moments that you are opening yourself up to by putting yourself out there dating, but believe me, the right person is worth it! Do it for them.

  • avatar Christy March 15, 2011, 3:45 pm

    Wendy, this was exactly what I needed to see! The tips on online dating are especially good–I’m trying it out right now, but I’m still so unsure of what I should be doing–how many messages to send, etc. (Mayhaps a column about online dating ettiquete?) Thanks!

  • avatar Jessica March 15, 2011, 4:02 pm

    Before I even read this, I just HAVE to comment… hilarious picture. Makes me laugh!!!

  • avatar Laurel March 15, 2011, 4:07 pm

    This is a really wonderfully written response, Wendy! (Also, the click through links don’t work.)

    LW, one thing I’ve found (since I’m usually awkward and nervous during the first few dates) is that “activity” dates are a lot less pressure and more fun than dinner dates where you have to make conversation all night. Coffee is good for a first date to see if you click in person, but activities like going to a park, hiking, some sports (I think tennis and racquetball are good for dates), visiting botanical gardens, going to museums, bowling, going to sporting events (more fun than going to a movie, I think), arcades and so on make for fun dates. Suss out what kind of activities your date likes and then try to plan an activity-date around that.

    • avatar sarolabelle March 15, 2011, 4:11 pm

      it’s because they don’t have the http://www. in front of them so Word Press thinks it is an internal link

    • Dear Wendy Wendy March 15, 2011, 4:16 pm

      Thanks, I’ll fix the links.

  • avatar Jess March 15, 2011, 8:43 pm

    One note on the stretch marks: my boyfriend used to be overweight and lost a good amount of it before we started dating. I think he has more of an issue with how he looks than I ever will and I never noticed the marks on his side until he pointed them out. No one but you will know that you ever were less than confident with how you look.

  • avatar Madi March 15, 2011, 8:53 pm

    I wish all the guys doing online dating would read Wendy’s advice – after 3 emails back and forth, ask for a date! I’ve been trying the online dating thing for about half a year, and most guys exchange quite a few emails back and forth, over the course of about two weeks, with no definite plans to meet. Two weeks is my threshold… I definitely think something is fishy when they don’t even ask for my phone number after one week. So LW, here are just two mistakes that turn some women off. Of course, you would have to ask for her number and for a date, and not sound too aggressive at the same time. Women expect you to ask for their number, and ask for a date. That’s why they are on the website!!!

    And to take off some of the nervousness – she will be nervous too. A meeting between two nervous people won’t end well, so why sweat it?

    I would suggest maybe call her before the date, but keep it short. You want to build up the excitement of you two meeting each other, not wear it off before you lay eyes on each other.

    It would really help if you live in a big town – you have more women to choose from. Make sure you schedule at least one date a week. And after the date, don’t sweat it.

    It’s usually nice to send a message back, saying you had fun, but you don’t think you’re a match, if you don’t feel like seeing that person again. It’s just polite, and she won’t be left hanging :).

    And if you really like her, and would like to see her again, make plans before the end of the first date. (No, this is not from personal experience :), but from the advice on this site a few days ago)

    As a fellow online dater, I’m just telling you what I’d like a guy to do. Or what I’d be comfortable with a guy doing. I’m still single, so I don’t know if it actually works :).

    Best of luck!

    • avatar Fairhaired Child March 15, 2011, 10:25 pm

      I disaggree – I think that a lot of women would feel uncomfortable about giving out their phone number in only 2 weeks – especially if they live alone. I would much rather make a date through email and do the whole “I’m going to be wearing a red rose and carrying a book” thing. Maybe after a month I’d be comfortable to make sure that there aren’t any red flags about them being a clingon/stalker personality.

      If the LW wants to offer up his number first that could be a different story so that each woman he gives it to can figure out her own comfort level with contacting him.

      Plus now in days most phones also are able to access email so they can just state “I’ll send you an email when I am leaving/get there” etc.

      One way to “avoid weirdos” having your number is to have a google voice account which can filter calls so that they may have your google number but not your actual phone number- which is much easier to block/cancel than a cell phone.

      • avatar Jess March 16, 2011, 8:18 am

        I can’t imagine going on a date with someone I’ve never spoken on the phone to. Meeting in person seems like a waste of time and money if the conversation doesn’t flow over the phone.

        Also I’ve never had any weirdos that didn’t go away after a few days of ignoring their calls (and even that was only like 2 or 3 guys who I gave my number to while drunks, whoops!)

        So I guess its just a personal preference

      • avatar Madi March 16, 2011, 11:36 am

        @Fairhaired Child – I think the days of “I’m going to be wearing a red rose and carrying a book” thing are long gone, in the days of online dating. I wouldn’t go on a date with someone who doesn’t have a profile picture on the website. I posted my picture, he knows what I look like, he would have to reciprocate by letting me know what he looks like.

        About the phone number – Jess mentioned it, but I forgot to – yes, I use a Google voice number. I made the mistake of giving my real phone number to a weirdo who kept texting me, even calling me 4 months later, after I told him I’m not interested. So LW, proceed with caution.

        I also have a separate email account just for this kind of thing. I don’t use my regular email account, for the same reason I don’t give out my real phone number – in case I meet a stalker, I can very easily get a new email address. Do not give out your work email, under any circumstances.

        This should go without saying – don’t ask women at your place after the first date. (Women careful about their safety would probably decline anyway.) You should figure out if she’s not a gold-digger, or who knows what other kind of weirdo.

        From what I’ve read, some guys are in relationships, but still looking for dates online. That’s why I have that two-week threshold. If the guy can’t find the time to meet me, if he’s not even excited/interested in meeting me, then he’s probably busy with someone else :). I am single, and I have time to meet new people. He should have time too. So LW, you would have to watch out for that too.

        Unfortunately, starting dating is just the beginning of your problems…

        • avatar Madi March 16, 2011, 11:45 am

          Oops – my bad – Fairhaired Child mentioned the google voice account, not Jess. Can’t modify my comment anymore.
          And we all have different levels of comfort – I’m comfortable giving my google voice number after one week. If someone else isn’t comfortable, then guess what? We won’t date :)

    • avatar Missy March 16, 2011, 12:10 am

      I actually agree with the 2 week rule. Through a lot of personal experience the men I met were either interested enough to meet as soon as possible or not interested enough in me to bother meeting within that 2 week time frame.

      Besides if you spend loads of time getting to know someone online, through email or just over the phone, the weirder the first (and subsequent) meetings/dates are. It’s almost as if you freak yourself out. Much easier to go in with a bit of knowledge, not too little, not to much.

      And as for safety taking the woman’s lead is key. My boyfriend has told me he met several women who didn’t even want to give out an email address before meeting nevermind a phone number. But I gave him my phone number in our first IM conversation – I hate getting to know someone through email. And I’m not the only one. So leave that up to her so that she feels comfortable.

  • avatar silvii March 15, 2011, 10:00 pm

    Hey LW. Firstly everyone gets nervous on a first date. I’m not saying I’ve date the whole of my shire (UK reference for you there!) but every time I’ve been on a first date, I had to have a dutch courage drink with one of my friends before going on my merry way. Yet chances are, the lucky lady will also be nervous – something you’ll both have in common straight away!

    I also wouldn’t worry so much about being inexperienced at your age. You sound like a sweet guy and I’m sure with a woman that deserves you, she’ll be sympathetic and considerate to what you went through as a teenager. When asking someone out, don’t be deterred if you get rejected. If this puts it into perspective, you wouldn’t necessarily go out with every woman on the street, would you! Just keep going out, meeting new people, perfecting your conversation skills and being you.

    I wish you luck in dating world and I hope you just have fun meeting people.

  • avatar lee March 16, 2011, 2:24 am

    Aww, I have no helpful advice to add, LW, as I’m kind of in a similar boat/can see myself heading in the same direction, I just wanted to wish you the best of luck! And honestly, as someone who was heavier but has lost weight too, don’t worry about the stretch marks or whatever, even skinny people have them and I know many girls who actually find them cute on their guys. Once again, best of luck! <3

  • avatar anna728 March 16, 2011, 2:36 am

    With both this and the girl a while ago who had never been on a date, I wonder, are there any dating sites for people who are new to dating? There seem to be all kinds of niche dating sites, after all.

  • avatar cdj0815 March 16, 2011, 8:00 am

    Everyone here has given such wonderful advice. Also LW everyone of us has something about our body that makes us a little self conconscience. Believe me, whoever you meet is just as nervous as you are, but just as interested in desiring to meet a wonderful guy. So hang in there and lots of luck!

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