“I’m 30 and Have Never Had a Boyfriend”

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I just turned 30 and I’ve never had a boyfriend — not even an unserious one. I fell in love with a boy in high school, and a boy in college, and…that was it. Just fell in love — as their friend — but didn’t date either of them because they weren’t interested in dating me (trust me, I tried, I really did). And I haven’t dated all that much. I could blame that on spending my formative years in evangelical Christians circles, where one usually ends up dating a member of that circle, and that just never happened to/for me. But knowing you appreciate honesty, I know it’s not entirely circumstantial. A part of it has been me and my own fears of intimacy, rejection, self-worth issues, etc.

I am 30 and have never had a boyfriend, and have never even been kissed. And for most women my age, this is, indeed, unique (though I’m hoping not as unique as I think, fingers crossed). I have profiles on various dating apps, and recently went on a very successful first date with a guy from one of these apps. We laughed A LOT and now I’ve been asked on a second date. I’m not gonna lie: I’m all giddy and happy and just mush. I really like this guy.

But my nerves are also kind of shot about the whole thing. What if he goes in for a kiss? How will I react? What if I kiss badly? What if I’m so nervous I pull a Ross/Rachel first time scenario and just laugh at the situation and he thinks it’s him? What if my breath stinks? I don’t know how to go on a second date. I don’t know how I got through the first! Was I this nervous for the first? What if we’ve already run out of things to talk about? What if…

As you can see, I’m…spiraling. Any advice you have for me to help me not spiral would be more than a little fantastic. For right now, I’m trying to bear in mind what my goal is for the second date, what I want out of the situation in general, working out how/what I might possibly feel for this guy…all while trying to enjoy what’s happening. (Can you tell I’m a victim of over-thinking?). — Reformed Evangelical Dater

First of all, I promise there are more people than you think who have made it through most — or even all — of their 20s without much — or any — dating experience. I get letters from them all the time. Here are three that I have published and answered:

“I’m 32 and Have Never Kissed a Girl”

“I’m 30 And Have Never Had A Date!”

“I’m 26 and Never Kissed a Woman”

You know what all of you have in common, besides a lack of dating experience and some self-esteem issues? You’re all overly concerned about what potential dates might think of you. You’re missing a very key part of the dating process: what do you think about the person you’re out with? If that sounds overly simple, it’s because it IS simple. The purpose of first — and second and third — dates is not just to see if there’s chemistry, but to get to know one another so you tell whether you even like the other person. How can you do that if you’re focusing all your energy on your breath? Girl, pop an Altoid and get on with it. There are more important things to figure out.

For some practical tips on easing your anxiety, re-read those columns I linked to above, and remind yourself that you aren’t a freak just because you’re 30 and haven’t had a boyfriend. And that anxiety you’re feeling about your next date and hoping it all goes well and you have enough to talk about and you say the right things and don’t mess up your first kiss, etc., etc.? Yeah, welcome to the club. I don’t care if you’ve had no boyfriends or 50 boyfriends, that anxiety is always there a little bit. All that means is you’re human.


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


  1. kerrycontrary says:

    When I’m nervous about something I tell myself “what’s the worse that can happen?”, and then I actually consider the situation. For the LW, imagine that your 2nd date goes horribly wrong and you spill soda on your dress, the guy is really rude and you actually don’t like him, and he tries to kiss you but then runs away because your breath stinks. So what happens? You go to bed, you get up the next day, and you keep on living your life as you have for the past 30 years.

    Being embarrassed or rejected will not kill you, harm you (besides bruising your ego), and shouldn’t affect the long-term output of your life. In fact, rejection is GOOD for people to experience because then you know how to move past it. You may need to go on 50 dates before you find someone good, but you will live and you will learn through those experiences. You will most likely collect some crazy stories to tell your friends over dinner. You may find out how truly WEIRD some men are. Don’t be so paralyzed by fear that you miss out on finding love.

  2. I was 31 before I kissed anyone and 33 before I found my first legit boyfriend (although there were a bunch of bad dates/uncommitted guys/losers between 31 and 33). You can do it! It sounds like this guy likes you, so yay!

    I’d encourage you to keep your expectations low. A kiss, another fun date. Don’t start running your brain toward marriage and kids and meeting your family just yet. (So easy to do.) Also, you can, like Wendy said, get so excited at the thought that a guy finally likes you, that you forget to see if you like him. And then you start making crazy plans for the future in your head…just be a little careful. And remember, either for now or in the future, that just because a guy wants to sleep with you doesn’t mean you have to. (This is something I wish I would’ve learned sooner.)

    I’d tell you, using evangelical language, to guard your heart, but I would be hypocritical, because I definitely didn’t do that and got my heart broken a couple of times, and bruised a couple of more. It’s just part of the deal.

    But don’t worry too much about your kiss. Kissing is something you can catch on to pretty quickly. For me the hardest part was knowing when he was going to do it and making myself available to kiss! I was quick to shut things down and go, because I was nervous and stuff. Also clueless. So if you’re sitting somewhere, and it gets quiet, that’s kissing time! If you want it to happen, keep yourself turned toward him, be smiling, friendly and open. Don’t seem closed off or in a rush to leave. And remember: you can stop things whenever you want to.

    1. I love your second paragraph and that’s why I wanted to tell the LW as well.

      LW, I’ve been dating since I was 17 and I’ve had several serious boyfriends. Even now, though, I’m anxious those first few dates and I start freaking out. I liked him? Does he like me? What does he think about me?

      One thing my therapist told me, and it has helped tremendously, is to take each date one at a time. Meaning, don’t start planning your future with this guy. Go on one date. See how it goes. Go on the next. Then the next.

      As for kissing, I remember my first kiss. I was 17. It was a little awkward, but I managed. So will you. Just let it happen. And the more you do it, the easier it becomes!

  3. artsygirl says:

    LW – I suggest you do a daily affirmation in front of a mirror. Highlight why you are a valuable person, be it you willingness to listen, your volunteer work, etc. Say it out loud and with conviction. The more you think about your contributions and positive qualities the more your confidence will grow.

  4. Skyblossom says:

    It might help to think of it from his point of view. He’ll be as worried about his breath as you are about yours and he’ll be worried about whether you like the place he chooses to take you and whether you want him to kiss you. Anxiety is just part of the situation at this point.

  5. Avatar photo gillociraptor says:

    Was this already posted?

    1. Yeah, last week for about an hour. Then it disappeared and the letter from the mom with the pervert shower-picture-taking husband appeared.

      1. Avatar photo gillociraptor says:

        Thanks! I was just confused.

    2. I did have it up for half an hour by mistake. I meant to schedule it for today, so here it is.

      1. Avatar photo gillociraptor says:

        Thanks! And now I feel all important because you replied to me.

  6. LW, there are some different ways to look at this. So, yes, you’ve never had a boyfriend. But you know what that also means? That means you’ve never had a terrible romantic relationship, or let yourself been treated badly by a boyfriend, or dragged on something for years when it should have ended earlier. Most of us who have had boyfriends probably would like to forget some of them. I definitely have some “relationship scars” I prefer not to remember. When you find a great guy to be your boyfriend, you’ll be a whole lot wiser than I was when I got my first boyfriend. Your situation definitely has its pros.

    1. I completely agree. It sucks a lot worse to try to decipher the crazy dating world after having your heart broken, because then instead of “What if he doesn’t want to kiss me because I have dragon breath?” you end up thinking “What if he continues acting great towards me just long enough to get laid and then turns into the most unbelievable ass I’ve ever met?” or “What if we end up dating for a really long time and he never wants to get married?” After the relationship scars are burned into your skin, the what ifs don’t get better; they get worse.

  7. Dude, my first kiss happened by surprise, in the dark, at 3 AM. I was 22. The girl I had just started dating kissed me as I left the bathroom and I was completely blind because the hallway was dark. I literally walked into her face. It was adorable for a first kiss. (Hint: All first kisses are adorable, given enough time. Tragedy+time=comedy.) It didn’t end up working between the two of us because we were both too nervous and fumbling.

    Once you get that first kiss done with, and that first-person-kissed done with, it’s much easier. It’s not as fraught with expectation and nerves. (Let’s be honest, I had to down a friend’s beer to get the ovaries to kiss my current gf, but it STILL wasn’t as stressful as that first kiss.) And the first time my gf and I french-kissed, I kinda pulled my head back and said “Man, tongues feel weird.” So like, even if it’s awkward, it can work out.

    1. Avatar photo Addie Pray says:

      ha, “tragedy + time = comedy” – very true!

  8. If you think the first kiss did not go as well as you had hoped (or, if it did!), you can always smile and say something like, “Can we try that again?”

    I guarantee it will work.


  9. Avatar photo Addie Pray says:

    My first kiss was awful. The boy slipped his tongue in my mouth and I gagged a little and yelled “ewww, you used your tongue!” He made fun of me for that and told others, and I didn’t get to kiss a boy for another 3 years. At that time, I was all about the tongue. Maybe a little too much – I think I knocked a few of my kissing buddy’s teeth loose. He had to pull away and actually tell me “easy with the tongue.” It was another 2 years after that before I kissed again – and by then I had found my groove. For most people, I promise it doesn’t take 5 years. So, if/when he goes in for the kiss, maybe shoot for somewhere in the middle of my two first kisses. But rest assured even if you are a bad kisser – even if you’re a bad kisser for 5 years like I was – there is still hope: you can still become The. Best. Kisser. Ever. you know, like I am now. If I do say so myself. Tra la la tee da.

    1. Ugh, my 1st was pretty awful as well. He did the dead tongue thing. And kept his eyes open (I may have snuck a peek), and it was in the front of my house, so I was scared my parents were going to walk in hahaha.

      1. My first kiss was terrible too! The guy caught me off guard. I didn’t even want to kiss him.

    2. My first kiss was so gross. He literally stuck his whole tongue in my mouth and moved it all around. YUCK. I still hate kissing with tongue because of that experience!!

    3. Ha. I love first kiss stories. 🙂 Mine was awful, too, everyone! I was watching TV/cuddling with the guy I had a crush on at 18. I had never cuddled before, let alone been kissed. I fell asleep and woke up to him kissing me! He wasn’t trying to be creepy, btw — I think he was going for something really romantic and Sleeping Beauty-esque, but when I typed that all I could think was, “Wow, what a creeper!” In any case, all I could say was, “Umm, umm, umm.” I was completely taken by surprise, didn’t even see it coming a little bit because, y’know, I’d fallen asleep! What ensued was an awkward conversation about how I was, like, totally into him and at 18, I was an idiot and thought that him kissing me meant he CLEARLY wanted to be my boyfriend ASAP. He did not, even a little bit, but he explained to me that “we could still make out ‘n’ stuff…” I was crushed. Now I look back and laugh.

    4. My first kiss, i was in junior high and was walking home w/ a group of friends, one of which was a guy i liked. We were playing truth or dare, and he dared me to kiss him. Of course i did, just a chaste kiss on the lips and he licked his lips and said “tastes like cherry”. I of course corrected him with “No, my sucker is strawberry” and then everybody laughed at me ’cause it’s not what he meant. Silly junior high.

    5. LOL. My first kiss was pretty awful too; it was post-homecoming dance and I hadn’t even come to the dance with a date. He was drunk and I gave him a ride home, which apparently in 16-year old boy language meant he was entitled to try a surprise makeout session. It was wayyy too much tongue and too sudden. After that, it never happened again til college when I met my first boyfriend and everything went much more smoothly in my college days.

    6. My first kiss… I was 13 and he was 15, a grade above me. We were in the family room watching Braveheart, our second date. I don’t remember exactly what led up to it, but he went in for it, and within moments, had his hand on the crotch of my jeans and was wiggling it fervently. And I just went with it because I had NO IDEA what to do. Crotch-grabbing was completely alien to me, I did not know why he did it or why anyone would do it. I knew about sex, just not a lot of the other stuff that leads up to it!

      Looking back now at the first kiss, and at the 8-month “relationship” as a whole, I can’t help gagging. And feeling really sorry for my clueless 13-year-old self (who thought she was soooo mature and ready for a boyfriend). He was the first boy who had really shown an interest in me so I was riding that self-esteem boost, ignoring red flags and conducting myself very poorly along the way, as if I were trying to get all of my relationship mistakes out of the way at once. The relationship was just messed up from start to finish – it finished when I tried to dump him, he said he’d kill himself if I did, so I decided OK, I’ll just cheat on him until HE breaks up with ME! Genius! *facepalm*

      LW, be glad your first kiss won’t be with a 15-year-old pervy loser. Seriously, once the first kiss is over, you’ll probably be questioning why you were ever worried about it to begin with.

      1. Oh, I told you how it ended, but how it started is just as good – He was really interested in dating my friend who lived near him and rode his bus, but she didn’t like him that way, so she pushed him over to me and he seemed OK with the runner-up arrangement. Yuck yuck yuck. I want to go back in time and shake some sense into 13-year-old KKZ!

    7. My first Kiss was funny too! I was 13 and I was “dating” this boy. I just knew he was going to kiss me. we were walking in this park and on a bridge overlooking a stream. I thought the setting was perfect for it to happen. I waited and then…nothing. I said to him twice “Isn’t this so romantic.” He just stared at me. So finally, I grabbed his head with both my hands and pulled his head to me. It was a surprised closed mouth kiss. I then let him go and stormed off. I was so mad that he didn’t do it. He then studdered after me going “That was great. lets do it again” And I was like, ” That was the perfect moment and you ruined it.”

      So LW, don’t get too in your head about the perfect kiss.

  10. I didn’t have my first kiss until 18. It came as a complete surprise and it was plain awkward. The good news is that unless you try to do something “fancy” like shove your tongue down his throat the first time, he will probably never know it’s your first kiss unless you tell him. And after that first one, it stops seeming so weird/it’s something that I think comes pretty naturally. It’s kinda like, “Oh, that’s what kissing is like? Oh, okay. Cool.” So, don’t worry too much about what to expect or how you’ll react. If you’re worried, just make the first kiss short! And, you can prep your breath by carrying some mints with you! 🙂

    I think what Wendy said is most important, though. Just as much as you’re worried about this guy sizing you up, you should be doing the same for him. Do you enjoy his company? Do you have chemistry? Does he treat you well?

    P.S. I laughed the first time I had sex with my first legitimate boyfriend (almost 5 years and a dozen failed kinda-relationships and/or weird men after that awkward first kiss). That relationship lasted a few years. Don’t worry about that Ross/Rachel moment, because I had one in a super intimate moment. Awk-ward! But, the point is, the right guy won’t care about any of this. He won’t care if you’ve never been kissed, or that you haven’t dated much, or if you have a silly moment and start laughing (as long as it’s clear that you’re not laughing AT HIM).

    1. Yeah, I would think a more chaste kiss is a good idea for the first kiss.

      And all this talk about first kisses is kind of making me miss that feeling of anticipation when you´re about to kiss someone for the 1st time.

    2. Also, I’m not sure if my gf and I have ever had sex without laughing.

  11. the other guy says:

    Good luck with your second date, strictly speaking you can put off having sex until your 3rd date, if you are under 30…. How old were you again. 🙂

    1. Sue Jones says:

      Um… I don’t think that was helpful!

    2. Don’t even joke! Poor thing is worried about kissing. Don’t worry LW – you’ll be fine – just have fun and put the whole kissing thing out of your mind. Focus on getting to know the guy and trying to have as much fun as you can. I promise you the kissing thing will work itself out on its own. My only advice for when it happens is to keep it simple – I just remember seeing a trailer for some reality show where two people who never kissed anyone before got married to each other and had the most awkward first kiss at the alter- in front of their families – it looked like they were down right hungry. Um – so don’t do THAT – for your first kiss less is definitely better than more.

      1. WFSS. Take it one step at a time LW; sex can be postponed indefinitely, the right guy will wait until you´re ready.

      2. That actually caused me physical pain.

      3. Me too – that one and the Liza Minnelli one when she married David Gest. Actually any one that tries to be so passionate…. in public in front of your family.

        My best friend was hilarious at her wedding and actually pulled away from the groom at the “you may now kiss the bride” part since her father was sitting in the front row and you do NOT kiss in front of your parents! The whole reception was devoted to mocking the poor groom!

    3. SweetPeaG says:

      I wasn’t sure what the other guy was trying to say here. But… agree… don’t make it worse for the LW.

      LW, don’t worry about the sex part. One step at a time, seriously. Intimacy at whatever level you choose will happen when you and the person of your choosing both feel comfortable enough. And it will all turn out just fine. For now, enjoy dating! There is a lot of fun to be had in going on dates. Don’t rush or take for granted any of the steps on your journey!

    4. Strictly speaking, you can put off having sex as long as you want.

      1. yay!!! you decided to keep commenting!

      2. Yeah, it’s weird participating, and i’m afraid i’m going to come across as dumb or something but so far so good.:)

  12. I love the advice to remember that you’re trying to figure out if YOU like your date. The very first time I did an in-person meeting with someone online, I was SO concerned with being likable that I didn’t notice that I didn’t like him… until the 2nd date. And then I realized that I didn’t just not like him, but I didn’t like him enough to leave early under the guise of needing to do laundry.

    Also, I’m 30 and I have had many boyfriends and dates and first kisses, and I just met a new guy that makes me giddy and we’ve been out TWO WHOLE TIMES and I’m an anxious insecure wreck! And we haven’t kissed yet and BELIEVE ME, I’m obsessing about it and, at times, spiraling. 🙂

    1. Avatar photo Addie Pray says:

      Oh you sweet young kids. It’s hard to remember those initial days with my boyfriend because they were SOOOOO long ago. …. Except they were only 2 months ago and I remember them vividly – I really worked myself up into a frenzy worrying about whether and when we’d go out again and if he liked me and blah blah. God, I did not like those first few weeks – too much anxiety for me. I can’t stand the “not knowing” part – you know, when you don’t know if they’re going to just decide “eh, not feeling it” and let it fade. Sick sick sick. I’m hyperventilating just thinking about it. I really sucked at remaining calm during those times. I’m glad my boyfriend of two WHOLE months – officialy, two WHOLE months today – well, fine, assmunches, I’ve known him for two WHOLE months – we’ve been official for just a couple weeks shy of that. God, that is not a long time. How have we moved so far, so fast? I was going to say something, Cats, and now I forgot. It was really enlightening and it was about YOU and not ME. Too bad, it was really going to change your life it was that good. But I forgot. So I’ll just end with this: My boyfriend is so fucking sweet I can’t stand it!

      1. Haha oh AP you remind me of when I first met my husband. I remember going from just getting to know him to two months and not being able to remember life before him. At the time I felt kind of crazy because it was going so fast, but I also didn’t want it to stop. Sometimes when it’s meant to be, it just works out. I think age plays a factor to. At this point you know what you want and when it’s there, you just want to grab it.

        Also our first kiss was on new year’s eve. It was our third date and I was so nervous I thought I was going to throw up. I mean not only was it our third date but there was a scheduled time for a kiss. Talk about stressing out, thank goodness for champagne!!!

      2. I’m bad at staying calm. And my mind is racing into the future like a crazy person. And over the weekend I turned into Drunk Texty-McGee and kept texting him even though he wasn’t responding, and then started using ALL CAPS because surely he’ll notice me if I use all caps? Oh god. Luckily he said it was cute. He said “Sorry I wasn’t awake for your drunk texts.” teehee. He’s so nice and cute and sweet.

      3. Oh god maybe he said it was cute but really he hates me now! I sent him a text at 10:46am and now it’s 11:37 and still nothing!


  13. Avatar photo thewriteway says:

    Oh, gosh, I know this feeling. I’m 27 and have never been kissed or had a boyfriend. I have been on dates and talked to guys, so I’m not a total hermit or anything, but I just haven’t found anything that clicks yet. I’ve done the online dating thing, but didn’t really get much out of it, and when I asked one of my recently married guy friends to set me up because he said he had a lot of single friends, he had no idea who to set me up with! So frustrating. And I tend to worry too much about whether or not a guy likes me rather than if I like him. Although I will say that I’m a little uptight because I have a history of divorce in my family. My mom has been there twice, my aunt went through it once and my sister is in the process of getting her divorce proceedings started. Needless to say, if I am going to do it, I want to do it right, which makes me more particular and weary than most.

    1. Just remember that just because you’re dating someone, even seriously dating someone, doesn’t mean you have to marry them. (I struggle with this sometimes.)

    2. Oh writeway, don’t even think about divorce/marriage yet! I know it’s hard sometimes if you are results focused – and I say this as someone results focused – but you can’t skip steps – even in your head. From my friends that date successfully, this is what I realized: The ONLY purpose of a date is to figure out if you want to spend more time with the guy. That is IT. There are some things in life where you can get away with putting the cart before the horse… dating usually isn’t one of them though. You can’t bring marriage/divorce into the equations until WAY later in the game – even in your head. I’ve had guy friends tell me they can sense when that is the end goal (as opposed to getting to know the guy) and then they bale because they feel the girl just wants them to step into a role that was already created before she met them. The difference for them really was ‘she wants to marry ME’ as opposed to ‘she wants to marry and I’ll do – even if it was I’ll do great’. Do you have a girlfriend that can be honest with you about your approach? Or a guy friend? It might be hard to hear if you put off a certain vibe you don’t think you are putting out – but it is better to know so you can fix it rather than sabotaging yourself. Some people are a slow burn rather than a snap decision – you kind of have to figure out how you think and see if that works for you or if you have to change your approach.

      1. Avatar photo thewriteway says:

        I have a couple of friends who aren’t afraid to be blunt with me, absolutely. One is a girl and a couple are guys, so I have a wide range of opinions to draw from.

        And yes, I am very results focused. I’m one of those people that wants to get everything right and be good at everything I set for; I pretty much hate to fail. I know it’s not the best outlook, but it’s hard to change.

      2. ele4phant says:

        I’m a results focused person too, but what I’ve learned is that relationships aren’t an end goal, nor are they a fail/succeed proposition. Relationships are never ending process, one that you have to work on day in and day out. Some days will be good, some days will be bad, but you’ll never reach a point where you say “Aha! I’m done. I’ve successfully built a relationship, now I’ll just put this in auto-drive for the rest of our lives.” If you don’t make the effort to focus on what’s right in front of you, or push to some arbitrary point in the future, things will fall apart. Changing your outlook is hard, and there’s no magic wisdom I can give you that will help you make this shift, you just have to constantly remind yourself of this, until it eventually becomes natural.

        And to another point, the end of a relationship (or rather, never having begun one) isn’t a failure. Don’t beat yourself up if it happens. You want to be with someone who will make you happy, and if that’s not possible with a particular person, ending the relationship is in both of your interests.

      3. I really like this advice, sometimes it can be easy to forget that all relationships are a never ending work in progress.

      4. Yep.

        This needs to become a dw-ism- ” relationships aren’t an end goal, nor are they a fail/succeed proposition. Relationships are never ending process, one that you have to work on day in and day out. Some days will be good, some days will be bad, but you’ll never reach a point where you say “Aha! I’m done. I’ve successfully built a relationship, now I’ll just put this in auto-drive for the rest of our lives.”

        Perhaps we could try to make it shorter, but I love it.

      5. Maybe “relationships, don’t drive themselves” or “relationships can’t be put in auto drive”

      6. I think you’re psyching yourself out too much. Try to remove dates from relationships. Some of my worst first dates were with men I was SURE were perfect for me and that I was going to have marriage baby montages with and some of the best dates were with men I knew nothing about. Made out with almost out of them though. Just remember that, kissing can be fun with with men who would be good boyfriends for you and with men you could never see yourself having a future with. I think you have to take that step to be ok with the chance that something can and will go wrong in dating, but you’re ready to jump in anyway.

      7. ele4phant says:

        So, I’ve had a thought that may work well for you. Try it on and see if it works for you.

        You say you are results oriented, so maybe you just need to shift what you consider a “success”. Instead of looking at a boyfriend or a marriage as a success, think of your personal happiness and fulfilment as being the goal. This gives you a much wider berth to claim victories than just chasing a relationship status.

        On a date, ask if yourself if you are having a good time and if you enjoy a guy’s company. If yes, guess what, a dating success! Don’t worry about what it means for the future, just enjoy that singular experience for the success that it was. If you’re in a relationship and its making you unhappy, well the “success” would be moving on, not staying in it so you won’t be single. Try reframing the goals you have for yourself away from just getting a partner to having a fulfilling life, and work towards achieving that.

      8. Word. I’m the same way, which is why I also fall in the 30-and-never-had-a-boyfriend category. I feel like

      9. … whatever guy I date, I need to know that it’s going somewhere. I like having a plan, so taking risks (especially with my heart) is something I’ve never done. Definitely trying to work on that. And take dates as they come instead of looking at the bigger picture.

    3. ele4phant says:

      So, when I was younger, I would focus all of my energy on trying to get guys to like me. I’d spend so much energy and time thinking about whether or not they were into me, trying to give off the right impression or sell myself as the sort of girl they’d want. And invariably, when they weren’t interested in me, I’d be crushed.

      I was given the same advice Wendy gave the LW, to just focus on whether or not *I* actually liked the guy. It took a lot of conscious doing on my part, but I started going on dates with the thinking “Well, how can they impress *me*? What do *I* like about *them*? Do *I* feel a chemistry?” Sometimes I’d back slide into my old habits of trying to get them to like me, but eventually I was able to shift my thinking. And it was amazing, I stopped stressing, I wouldn’t get upset when guys who I obviously had nothing in common with weren’t interested, and I was relaxed enough that when I did met someone I clicked with, things were smooth sailing. There’s no magic formula to help you shift your outlook, you just have to repeatedly remind yourself to approach dating in this way until it happens naturally.

      Also, to get divorced you have to get married first. And to get married you have to have a serious relationship first. And to have a serious relationship you have to get to know someone first. Take it one step at a time, and don’t jump ahead multiple steps in your brain to somewhere you may never get with that particular person. Focus on dating and getting to know someone, focus on doing *that* right. For every step of the way, stay in the present. If you spend to much time worrying about a theoretical future that may never come to pass, you’ll neglect what you need to be focused on *now* to make a happy healthy relationship.

      1. Thanks. I needed ALL this. Thank you all.

  14. LW – Besides WWS… Relax! Just go with the flow of things and don’t stress! If push comes to shove, you can always tell your date the real deal on your dating experience. Don’t give away too much of yourself, but if you just relax and go with it and stop worrying so much about what he thinks of you (just an fyi… he must like you if he asked you out for a SECOND date…) and don’t worry about kisses. They come naturally and take practice like all new things. And sex… worry about it when you get there and you’re ready.

  15. I was 21 when I had my first kiss, and it was with a guy who I would have never gone out with now, but back then I was in *UNICORN WISHES LOVE* with him, simply because he liked me and wanted to date me when I was sure I was undateable. He was such a weird kisser. He just stuck his non moving tongue in my mouth like I was supposed to re-animate it or something and every 10 seconds or so of kissing he would stop and push his check into mine like we were 1940’s movie lovers, separated by this damn war.

    BUT, as weird as he was with that stuff, he was so gentle with how nervous I was. I was so shy I couldn’t even look at him. He just sweetly started to hold my hand, asked me if that was ok (I was so shy I could barely nod), put his hand in my hair, and he waited for me to get the nerve to look in his eye before his kissed me (he also kindly ignored that I was fire engine red). I remember that so fondly, because without knowing that I had never kissed anyone else, he knew to be sweet and slow with me because I just somehow exuded that I needed to be treated like that.

    After that, I kind of owned how shy I was with guys. I have never, to this day, made a move on a guy first. Every guy I’ve been with has had to do 90% of the work (thanks Hitch!) and I moved from being terrified that I was going to mess up kissing a guy, to LOVING that tense feeling waiting for a guy to kiss me. The guy you went out with is going to be more nervous about what he should or shouldn’t do, so try your best to enjoy that, because it is so.much.fun. watching a guy fidget like that.

    So here’s a couple tips from another late bloomer (who made up for time and then some with kissin since):

    1.Don’t put all your eggs in one make out basket with this guy. Keep looking for more dates no matter what happens on this date.

    2. At the same time, don’t think about how you should be, be how you are. Your confidence will inspire him to make a move on you. If he doesn’t make a move on you, it was nothing to do with you, only to do with his own issues.

    3. Embrace the awkwardness. Sit in a car with him or where ever until you run out of conversation and wait for those delicious weird silent moments where no one talks. That’s when the kissing happens. If good conversation happens forever, there’s no segue-way to make out time.

    4. Keep some mints in your pocket (although most guys will be too nervous thinking about their own breath).

    5. Kissing is crazy easy. Just don’t bite him…..yet.

    1. ele4phant says:

      “Kissing is crazy easy. Just don’t bite him…..yet.”

      Yep, for the first time just be conservative. Don’t try anything that 17 magazine says or some other girly magazine says makes a good kiss (like deeply jamming your tongue down his throat or biting his lip). Just lean in, touch your lips to his, and go with it. Its intimidating if you’ve never done it, but in all honesty, its not building a rocket ship, ya know? You have a wide margin of error. Even if its not the BEST KISS he’s ever had, as long as you don’t try anything waaaayyyyy out there, it’ll be just fine. And if you like each other enough, you’ll have plenty of time to practice and figure out what he (and you!) really enjoys.

      1. OMG, YES. I used to read those articles from Cosmo that said stuff like “circle your tongue over his teeth in a counterclockwise motion” like, for how long? A minute? Two hours? What if I do it clockwise? Will his boner die from sadness?

        All those tips should just make it simple like “Press into his mouth with your mouth. Do that for awhile. If he does something to your mouth you like, do it back. If you want him to go further, touch his crotch. Repeat”.

      2. ele4phant says:

        Haha, yes that’s really all it takes.

        And I think, for me at least, the best kisses I’ve had are not because of the dude’s awesome technique, but because *he* was awesome and somebody I really wanted to kiss. I don’t think I have any memories were I went out with a guy who I was ho-hum about but who’s kiss made me feel weak in the knees.

        LW, if you two are excited about each other, your kiss will be amazing. Just don’t go nutso trying to impress him with a bunch of tips you’ve picked up secondhand. As long as you don’t lick his face off, if he’s into you he’s going to be into the kiss you two share.

    2. Eagle Eye says:

      hahahahahaah, so funny story, for my first kiss with my now-boyfriend (of 3.5hrs) I TOTALLY gnawed on his face – to the point that he actually had scabs for a like a week!

      I was SUPER drunk and it was NOT classy but over three years later, I’m writing this on the couch while he’s working on our dining room table, so, honestly besides having one of the worst first kisses of all time – things have most definitely worked out!

  16. Wendy’s advice is great! I was 27 before I really started dating anyone. I was always so shy and I was convinced I was going to be alone forever. But, I found dating got easier the more I did it. Which I mean makes sense looking back but at the time I thought I would never succeed that I would somehow get an F in dating and be banned from it or something ridiculous.

    Just try and relax and have fun. And kissing is always awkward at first, but just tell yourself that despite the fact that at the moment you feel like you’re going to throw up, people do this for fun, and if you let yourself go and enjoy the moment you’ll have fun too.

  17. LW I will tell you a little story about myself that I hope will make you feel better. I was 19 and still a virgin and just decided one day that I didn’t want to be a virgin anymore. I knew this guy who had a crush on me so when he asked me out I said yes with the intention of having sex with him….but I was so nervous because I had zero experience and had no clue what to do…so the night of the “date” i drank half a 40 oz of vodka and we went for a drive (I was too drunk to actually go to a restaurant or public place)…anyways long story short we had sex and I thought he would never call me again…but the very next day he did…i’m not sure what my point to this is…just thought it might make you feel better to know that everyone is nervous when they date and there is a first time for everything (and everyone goes through it).

  18. Avatar photo bittergaymark says:

    Honestly? If you’re over 30 and never been kissed? Man or woman? Gay or straight?

    Do yourself a favor and go out and hire a professional and lose the fucking big V already.

    Why? It’s simply because until you do — you will manage to blow ANY date or even casual encounter you have because you are instantly overly invested in the outcome of whatever happens. You will judge every move you make to an absurd extreme — leaving you as a deer caught in headlights.

    Look, you are far too desperate at this point. And yes — I am being completely 100% serious here, too. Now go hire a pro and take the edge off… Otherwise, you might as well start writing that “I’m 35 and Have Never Had a Boyfriend” letter now….

    1. theattack says:

      Why would losing her virginity make her less invested in her dating life? She seems more concerned about having an emotional connection and a relationship than having sex, so she still could be overly invested in dates because of the relationship potential, not the sex potential.

    2. ele4phant says:

      Eh, I don’t think that idea will be all that helpful to the LW.

      Why? Because the “outcome” she is hoping for is an adult relationship, not turning in her v-card. I mean yeah, the first kiss and having sex for the first time are part of that, but they aren’t the main component. Getting physical experience will not help at all with the larger jitters of never having had a relationship. The physical part is not the part that’s freaking her about; its about all of it.

      And besides, there have been numerous posters here who have been in the same boat as the LW, and they haven’t had to resort to hiring a prostitute. It is possible that she can get herself in the right frame of mind not to blow it.

    3. Woahhhhh. Totally not helpful.

      1. Avatar photo bittergaymark says:

        Eh, worked for a straight male friend of mine…

      2. ele4phant says:

        Is it a safe assumption though that your friend just didn’t want to be a virgin anymore and wanted that weight off of his shoulders? He wasn’t necessarily starting to date someone he liked and worried that lack of experience was going to make him screw up whatever potential was there, was he?

      3. Avatar photo bittergaymark says:

        Actually, he was much more terrified that he would be a lousy kisser and what not. Right down to the 7th grader-ish breath fear… Meaning he was pretty much like the LW who devotes an entire paragraph to these exact same fears… My friend simply had ZERO confidence. And nobody, male or female ever really finds that remotely attractive… They just don’t.

      4. I think there’s a big gender difference there. Both in terms of self-perception and outward perception about being a virgin.

        Also, I think that hiring a professional is much more of an option for a man than it is for a woman. The world isn’t exactly crawling with straight male prostitutes.

    4. ele4phant says:

      Plus, she already has a guy in mind that she’s interested in (and seems to be interested in her). She doesn’t want to become sexually experienced just to pass that milestone, she wants to become confident to make it work with this particular guy.

      1. Avatar photo bittergaymark says:

        Well, when she completely BLOWS it with this latest guy due to acting like an eleven year old, I do certainly hopes she takes what I say into consideration. Honestly, I truly believe the only way to have confidence in your sexuality is to actually, you know, put it to use…

      2. I think there is some value to that–lord knows I was a wreck when my gf and I first got together. But at the same time, I don’t think sleeping with a random would have actually helped me. I think it just would have made my self-esteem even worse. Maybe a sex surrogate? MAYBE?

  19. Getting laid by a hooker won’t help her have confidence when she’s with someone she’s not paying to be with her.

    I mean, if she’s concerned ONLY bout logistics, that’s one thing. But that’s not the deal with this LW.

  20. I had this same mindset when I turned in my v-card. (Not to hire a professsional, but to just lose it and get it over with.) It was so…not. I wish I could do it again. Maybe I should’ve hired a professional. Seriously, LW, do it when you’re ready and for the right reason.

    1. ele4phant says:

      Me too. The first time was with someone I didn’t really care about and I just wanted to get it over with to get it over with.

      It was pretty bad. Its not a huge regret, I don’t carry around any shame about it, but if I knew then what I knew know I would’ve waited for someone I genuinely cared about to have my first sexual experience with.

      And you know what? I would still feel awkward and scared each time I first got with someone I really liked. Having had sex before didn’t necessarily make things less awkward, anxiety inducing, or make me feel anymore competent. Being nervous when you get naked for the first time in front of someone you care about is part of the game.

      1. I totally agree. It’s scary. And having a bad first time can definitely color your perception of sex. At least if I HAD hired a professional, it might’ve gone better.

  21. If the chemistry is working, being a “bad kisser” is fixable, and something people are willing to put time into in order to fix (it isn’t like kissing isn’t fun)… If the chemistry isn’t there, being a “good kisser” doesn’t help much (if any).

    If the chemistry works, a lot of this will sort itself out; if the relationship has mutual respect, mutual interests, and chemistry… you’ll be fine. If you don’t have those three, no amount of previous dating experience will save it.

  22. Oh, and I think it’s really hard to be an actively bad kisser when you’re just starting out when you’re older. Like, a boring kisser, perhaps, but you’ll learn from the person you’re kissing.

    1. Thats a great point, Christy.
      Also, with each person you kiss you pretty much start over, in terms of what kind of kiss the new person likes, so at least the LW has no bad habits to be broken out of. 🙂

  23. Laura Hope says:

    LW, a kiss can be like a dance. Let him lead. You can just follow until you figure out what you would like.

  24. SixtyFour says:

    Has “First Kiss” or “first sex” ever been a weekend open thread? Sounds like everyone has some really funny / awkawrd / sweet stories!

  25. LW, I feel you! I am a bit of a late-bloomer too. I dated a little in my early 20’s and had a boyfriend for awhile, but after we broke up I didn’t have another boyfriend or kiss anyone again for 7 years, until last year at 28. I thought I’d forget how to do it! But don’t worry, it really does come very naturally and is very easy – especially if you really like each other. With my ex (whom I still miss terribly, dangit), last year, I knew it was going to happen on our third date (which lasted all day) but it took him about 12 hours to get up the courage to kiss me – and then it was so sweet. It sounds cliche, but you really will know when it’s right, and then it will be lovely! I’m very excited for you. 🙂

  26. I am turning 33 years old and have never had a boyfriend. Well, I have dated, and had two situations that could have led to a interrelationship but sadly didn’t. The second situation really felt like we were headed toward having a relationship. We had made out a couple times and I thought: “Wow, I am heading to a relationship”, but it didn’t turn out that way. Even though he liked me as a person, he still didn’t want a relationship with me because he didn’t have time and felt that we were on two different paths (and we were). I felt crushed and taken for a ride. I couldn’t fathom how you could make out with someone and not want to a relationship. Now I have learned that when a guy kisses you, it doesn’t always mean he wants you as his girlfriend, but rather, he just wants to kiss you.

  27. Well, I know this is an old post but I wanted to say you are not alone. I’m a few weeks away from 30 and I’ve never had a relationship. I’ve had a few flings that’s lasted a couple of months but never past it. Never something where we were exclusives. I closed myself for years due to loosing my parents and even after I opened up, I blame my weight (I’m not obese but I’m chubby) on the fact that I’m single. It’s realky difficult to work on our self esteem and I hope to work even more on that soon.

  28. I’m 40 and have never had a girlfriend and still a virgin. My 1st kiss was my last kiss and my best kiss. I was a shy person so never stood a chance so gave up long ago.

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