“I’m 26 and Never Kissed a Woman”

I’m a 26-year-old man and I’ve never kissed a woman before. I’m not hideously ugly or anything like that; in fact, my best friend often tells me that when he introduces me to his female friends or girls in his family, they usually tell him afterward that I’m cute and ask if I have a girlfriend. My problem is that I just don’t know how to talk to women at all. One reason is because my father was an alcoholic who beat me, so the only way I could cope with that hell was to withdraw inward. Add to that the fact that my sister had a nervous breakdown and was in a mental hospital for months, and it was too damn much for me to deal with as a kid, let alone all the other angst of being a teen. As a result, my only interactions with women were kept strictly business/friend, never romantic. I never allowed myself to feel anything more than that because: 1) I was convinced no one would want a messed up loser like me; and 2) I was scared of being vulnerable.

Only relatively recently have I considered dating. I finally have a great job where I can support myself, and save up enough to support my sister in the future because it doesn’t seem like she will ever be able to take care of herself. I’ve gotten counseling and support from close friends and family, and am in generally a much better place than even just three years ago. Unfortunately, because of my past and choosing to be the complete opposite of my father, I have turned into the stereotypical “nice guy” who pretty much every girl says she wants, but ends up never going out with. So forget the bar scene entirely; I chose to start dating via Match.com.

So far, in the seven months I’ve been on the site, I’ve gone on three dates. As far as I’m concerned, that’s as big an achievement for me as flying to the moon was for the human race. My problem is that I was never comfortable on the dates because of this giant 800 lb. gorilla in the room. And of course it showed; I asked the women out for a second date, and all three times I got “You’re a nice guy and all, but…” And this is where I’m looking for your help; how in the world can I convey to the women on the site that I’m really not like most other guys there? Do I just tell the truth about my life story from the start? I fear that if I say that I’ve never kissed a woman, they’re all going to click “back” on the browser in a millisecond and never give me a chance. How do I write my profile to say that I’m probably going to be one of the nicest, and shyest, guys these women will ever meet, but without falling into the trap of being the “boring, unchallenging, nice guy”? What sort of things should I write, and how should I write them? How should I write an opening email to a woman I’m interested in on the site? I know it’s a lot of questions to ask, and I have hundreds more, but I really have zero experience when it comes to anything dating-related, so any advice you’d be willing to give would be fantastic. — Hopefully not 40-Year Old Virgin

It’s wonderful that you have risen above your messy childhood and are making something of yourself. It shows amazing character that you are actively planning for the long-term care of your sister. And it’s great that, despite your insecurities and lack of experience, you’re giving a real go at the whole dating thing. But, dude, if you’re going to be successful and find a good match for yourself, you’ve got to change your attitude — and fast!

First of all, it’s a myth that women aren’t into “nice guys.” As someone who married a “nice guy,” I PROMISE you that for many of us, there’s nothing hotter than a guy who’s got our back and makes us feel valued and respected. There are two secrets here to finding your match. First, you need to look for women with self-respect — they’re going to be the ones who are over the stupid game-playing and all the drama that comes from dating guys who treat them like shit. Second, you need to believe in yourself — believe you are and have something of value to offer the ladies. And you need to lead with that. Always, always, always lead with your strengths, not your flaws.

So, let’s start with that, shall we? Instead of telling women in your profile or on a first date that you’re inexperienced and you’ve never kissed a woman and your super shy and blah, blah, blah, focus on the stuff that you’re confident about — that you have a great job you love, and a solid group of friends, and you’re the kind of person people can turn to and depend on. Make a list of things you love about yourself and lead with all that. Better yet, hire me and I’ll help you compose your dating profile. We’ll get rid of all the stupid negatives you seem fixated on and package you as the amazing catch you are.

When it comes to first dates — or second or third dates — there is absolutely no reason you have to tell a woman you’ve never kissed anyone. I would NOT bring this up. I wouldn’t even think about it when you’re on a date. Instead, focus on getting to know her, asking her questions about herself, and sharing personal stories that give her a sense of who you are and what you’re looking for. Great first date topics include: what you like to do for fun; movies, books, and music you love; places you’ve visited; where you grew up and went to school; and goals you have for the future (“I’d love to start my own business in a few years,” or “I hope to run a half-marathon in six months.”). Stay away from awkward or painful topics until you are much more comfortable with each other: your alcoholic father and abusive childhood; your relationship and sexual inexperience; that time your sister walked in on your jerking off. Keep things light and neutral.

Dating isn’t rocket science. There’s really not a steep learning curve here. If you’re engaged in the world around you and you’ve managed to make it to 26 without being a total hermit, you already have dating skills and you don’t even know it. Dating is simply about getting to know other people and seeing if you have enough chemistry to invest time in each other’s company. Honestly, that’s all it is. You don’t have to have kissed a million girls to be able to do that. You’ve been doing it all your life. It’s how you make friends. It’s how you land jobs. The only difference with dating is that eventually you have to decide if you like each other enough and have enough chemistry to be physically intimate. You can decide that on date #1, or you can take your time. There are no rules. It’s about how you both feel. And if you want to kiss a girl and you think you’re getting some clues from her that she’d like you to, too — she’s been playing with her hair, making lots of eye contact, licking her lips, smiling a lot, and gently touching you when she’s talking — go for it! Lean in and give her a little peck. If she leans into you, take it a little deeper, pull her a little closer. If she’s resistant or turns away, no harm. Maybe you just read her signals wrong. Maybe she’s interested in you but not ready to kiss yet. Or maybe she’s just not feeling it. Whatever; who cares! You won’t have been the first person in the world to not be kissed back. It happens ALL THE TIME, and it’s not a big deal. It doesn’t mean you’re doomed to be single or that you’re not challenging enough or whatever other bullshit you’ve convinced yourself has made you undesirable. It simply means that this one woman in this particular moment wasn’t feeling exactly what you felt. So, move on. See if she wants to go out again and try it one more time. If not, tell her it was nice to meet her, wish her well and move on to the next woman. Because there will be a next woman. And as long as you keep trying and keep being yourself and having confidence that you are and have something of value to offer a woman, you’re going to find someone who wants to be with you. It will happen. There are women who want what you have. You just need to be clear about what it is you’re offering and quit focusing on what it is you aren’t. Capiche? Good.

*If you have a relationship/dating question I can help answer, send me your letters at wendy@dearwendy.com and be sure to follow me on Twitter.


  1. Really great reply Wendy! That’s all I’ve got to say… do what Wendy says 🙂

  2. I think you sound like an awesome person. The fact that you are even going to take care of your sister shows what a great guy you are. I am very sorry about your father and how he treated you, but give yourself props for not becoming like him! And who cares that you haven’t kissed anyone yet, there is a first time for everything, give it time it will happen. Don’t give up because you’ve gone on a few dates with people you didn’t click with. Keep dating around and eventually you will meet someone that you do click with!

  3. silver_dragon_girl says:

    Wendy’s advice is excellent. Dude, you are totally psyching yourself out. There are plenty of women out there looking for a nice guy. Don’t write yourself off based on three dates! And never, ever stop being yourself to try to attract women- that is how douchebags are born. I guarantee that if you stick with it, eventually you’ll get that second date. Then the third, and so on and so forth.

    By the way, I recommend hand-holding as a subtle “feeler” for whether or not to go for a kiss. Walk her to her door (or take her for a walk in the park as part of your second or third date or whatever) while holding her hand. If she goes for that without finding an excuse to pull away (looking for something in her purse, wrapping her arms around herself, adjusting her hair or clothing, etc.), it’s a pretty strong indicator that she’ll be into a kiss (not necessarily an all-out snog fest, but a nice peck on the lips or cheek).

    There is NOTHING wrong with taking it slow 🙂

  4. SpaceySteph says:

    Nice work Wendy. Love that end part about getting over the fear of rejection. I like to say that there’s only one way to have a successful relationships (one that ends with being together forever) so you have to get used to alot of unsuccessful ones first (first dates, third dates, year long relationships, etc.) Some think its a downer way to look at it, but I like to think that I’m not letting anyone down or sucking at life by getting dumped because it’ll be wrong a million times until its finally right.

    Also, a few years ago I had never kissed anyone and I lived my life petrified of kissing. Like I was stuck in middle school “ohmigod where do I put my hands should I close my eyes ew what does a tongue feel like” forever. But the truth is its totally not that scary or weird. I agree with Wendy, if you want to kiss her, give her a little (non scary) peck. If she wants more, chances are she’ll go for it. And then you don’t have the awkward conversation I subjected my first boyfriend to, about how I was scared of kissing and he should just sneak one in one day without warning me or I would probably freak out. Yes, it was totally romantic. :-/

    1. silver_dragon_girl says:

      Heh, that was me, too. I got over it by getting drunk and making out with a friend of a friend, but that was at age 22, long past the point at which I felt it was “normal” to be worrying about such things. We late bloomers always feel sooooo awkward! Then it finally happens and you realize it wasn’t that big of a deal at all…

    2. I was a late bloomer too! I didn’t have my first kiss until I was 21, and lo and behold it happened when I was drunk, and there was nothing to worry about – it just came naturally to me. No worries, chances are when you do get that kiss, they won’t be able to tell it’s your first time.

    3. SpyGlassez says:

      Got ya all beat. I was a late bloomer at 28 when I first kissed my boyfriend (of almost 2 years now).

  5. Really great advice! And I promise that girls date “nice guys”. I date a nice guys, but I don’t date boring guys, and it doesn’t seem like you are very boring! You just need to the confidence you possess in the other areas of your life to bleed into your dating life. I know a ton of people that were super shy or introverted and they have somehow ended up married before me! And its all because they met the right person. So you’ve gone on 3 dates with girls from match.com. It make take 25 dates! But that’s ok, just keep trying.

    1. i totally second this!

      i read a study once that said that people will fall in love 5 times before they find “the one”. whether thats true or not isn’t the point- the point is that it will definitely take more then one try! nothing in life is just handed to you at your first try. jobs don’t work like that, houses don’t work like that, friends don’t work like that- why would dating work like that?

  6. melikeycheesecake says:

    Wendy hit the nail on the head…. Listen to her.. 100% listen to her.

  7. Buzzelbee says:

    LW, women do like nice guys! I fully agree with all Wendy said and I married my wonderful husband because, among other things, he is such a nice, kind, thoughful man. Give yourself and all the women who would love to be with you a chance.

  8. I agree with all of the above, and I have a couple things to add that might help. When you’re talking with your date, ask her meaningful, open-ended questions and allow her to respond. For example, “What do you find most rewarding about your career in _____?” or “I noticed that you mentioned you enjoy surfing; how did you become interested in that hobby?” Let her answer, and listen. You then have the opportunity to share a little bit about yourself that mirrors what she’s just said. If she says she finds being able to help others the most rewarding part of her career, take the opportunity to tell her a little bit about how you enjoy your work volunteering at _____ organization for the same reason. By doing that, you are establishing what you have in common and becoming more comfortable with each other. Ultimately, as Wendy said, dating is a lot like friendship in that you have to establish that you have enough common ground to continue enjoying each other’s company.

    Hand-holding is a great way to subtely figure out if a woman is interested in more physical contact. Also, it’s kind of romantic and sweet to go for that first. It shows that you’re interested, but that you aren’t pushing your own agenda right away. A hug and a kiss on the cheek is another good way to go, especially if the hand-holding went well.

    Just be confident in who you are and how far you’ve come in working through the traumatic experiences you’ve had. You will eventually find someone who is happy to have such a caring, thoughtful relationship partner. Good luck!

  9. And remember, self-confidence is one of the most attractive traits a person can possess.

  10. Three dates is a great start; the best way to become less uncomfortable is to just keep going on dates.

    Also, I think it’s okay to let dates know you’re “inexperienced”, without getting into the gory details right away.

  11. Great advice from Wendy.

    Sounds like you have your shit together dude. That goes a long way with women in itself. Chin up and keep going on those dates – you’ll click with someone eventually. Love is a numbers game.

    And about the kissing…most people don’t care how inexperienced someone is if they like them.

  12. Dear LW, listen to Wendy!! And don’t drag that 800-lb gorilla named “My Past” on your dates with you.

    If you’re not getting second dates, don’t take the easy way out by telling yourself you’re too nice. You probably are very nice, but nice doesn’t drive good women away. Are you unconsciously acting uncomfortable when you’re on a date because you’re afraid the Horrible Truth About My Past will come spilling out inopportunely? Women are sensitive to non-verbal cues, so maybe your discomfort is making them uncomfortable in turn. If the first date doesn’t “feel right” women are unlikely to say yes to a second one, no matter how nice you are. Go back over your recent dates and look objectively at what you said, how you said it, what your body language was, what her body language was, etc. and see what you can learn to do better: just like any new skill, you have to review and practice.

    And instead of feeling like you have a huge negative boil waiting to be lanced with every single woman you date, take the attitude that your past is privileged information – not for the idle consumption of everyday Cinderellas who are just passing through – but reserved for someone who is earning your trust. Just like you, and like all of us, she will have her own past, insecurities, failings, and problems, and she will also be hoping to find someone trustworthy to share them with. And to kiss. Believe me, the kissing will take care of itself once you…er…get that monkey off your back..

    1. MiMi I love what you said in your last paragraph here, and wholeheartedly agree!

      LW, one thing that you never said when discussing getting a second date was whether you wanted to see these particular women again? Or did you simply want a 2nd date because it’s a goal independent of these women? Keep in mind, dating’s a two-way street, and you should be figuring out how YOU feel about THEM just as they’re doing with you. Take some of your power back in these situations and don’t take a scattershot approach.

  13. Wendy gave some great advice, but as another woman married to a nice guy, I wanted to make a distinction. Women like guys who are caring and nice, but they also need the guy to be confident and secure. Some guys only have the “caring and nice” part, and if that’s all that the woman thinks he has going for him, she might think he’s a doormat or desperate for attention, affirmation, etc. – that is not appealing, and is what women typically mean when they give the “You’re a nice guy, but…” explanation. 

    1. Eagle Eye says:

      This is so true, my boyfriend is a kind, thoughtful and loving individual – he’s the kind of person who notices that I always put blueberries in my cereal in the morning so when I’m running late for work, he’ll throw together my breakfast just the way I like it without me even asking him to (because he is just THAT adorable).

      But, he’s also no pushover – if he disagrees with me, if he thinks that for whatever reason he has a good idea that we should implement, then he’ll voice his opinion and stand by it confidently, so that I believe that I’m in relationship with my peer – someone who I believe I can lean on if I need to but also someone who can lean on me…

      Look for confident women who want someone to be their partner – they want someone loving and caring but also strong and supportive – all of which you seem to be!

  14. I completely agree with Wendy, AND ALL of the other commentors, i do have one question though. Say LW does exactly what he should do and go in fully confident and all, staying away from the “topic” that would make it possibly awkward. What IF the person he is going on the date with actually brings up the topic of kissing and physical intimacy, and possibly asks him what he likes in that department or any other questions in that area, how should he not become bright red and uncomfortable?

    1. I think you can mention that you’re “not very experienced” or that “it’s been a while.” Any intimate relationship, whether it’s your first one or not, involves a lot of exploration together. You both have to learn your likes, dislikes, and adaptations with each other. She may have been with other partners but it will still be new with you and you’ll both be figuring some things out… so try not to be intimidated. Learning together is part of the fun.

      Just don’t go into any detail about your experiences until it’s a serious relationship and you’re talking about your pasts. Like others mentioned, the right person won’t mind that you haven’t been with other women. Disclosing it on the first date would probably weird her out, but once she’s grown to really treasure your budding relationship you won’t scare her off. Many women put a lot of emotional emphasis on physical intimacy, so she will really value being able to share some firsts with you and knowing that she’s special enough for you to open up to.

      I think that sometimes our culture puts a lot of emphasis on sexual and romantic experience. On TV, virgins are punchlines and those who don’t date are sad, lonely losers. But real life is so much more varied and complex. I don’t think that a lack of experience is at all a barrier to developing a great fulfilling relationship. For some people it takes many years of dating, and for others one of their first partners ends up being their lifetime partner. Where you’ve been up to age 26 does not sabotage your future at all. In fact, your maturity and self-awareness are fantastic qualities.

      You obviously know that patience, strength, and effort pay off in life. You’re well on your way to some fun dates and wonderful relationships.

    2. Maintaining sang froid in the face of tacky inappropriate questions on an early date?
      How about giving a silent stare and then calling for the check?

  15. VioletLover says:

    Wendy is definitely right about the ‘nice guy’ myth. All the guys I’ve dated have been the ‘nice guy’. But think about what makes a dude a ‘nice guy’. They’re sweet, and caring, they’re friendly and funny. They love to see the person they’re with smile, and they’re incredibly supportive.

    Focus on THOSE features instead of just summing yourself up into a trite, two-word stereotype. You’re obviously a responsible guy (which is definitely attractive. Girls don’t want to be your mom). You’re willing, and able, to take care of your poor sister. That shows a good heart, and lets a lady know that if something happens to her, that you’ll be there for her.

    You’ve got the determination and motivation it takes to heal from a horrible past, and that shows that you’re able to handle what life throws at you. If you can rise above an abusive alcoholic for a father, it’s likely that you can handle other negative things, which shows that you’re a strong person.

    You just need to focus on those things as individual traits. That makes them stand out more in people’s minds.

  16. Try not to put too much pressure on yourself or your date. Consider each date as an opportunity to get to know someone, not the last chance possible to ever get kissed. Think about your ideal life partner. What characteristics would she have? Likes kids? Plays tennis? Loves reading? Make it your goal to find out what this person is like, and see if you can answer five or six of your ideal mate questions (too many and it will seem like an inquisition.) (And be sure you ask casually, rather than “I’m looking for a girl who loves Trollope. Is that you?”) Find out what she values or is looking for. Maybe she wants a guy who loves camping, and that is, is not or could be you. At the end of the night, you should have an idea of whether she’s someone you’d like to get to know better. If so, ask her out. She may say yes. She may have decided that you’re not someone she’d like to get to know better. Perhaps hating camping is a dealbreaker. Perhaps you mentioned your love of travel and she’s a homebody. If you don’t match, it’s not because either of you are defective. You’re just not a good match. And don’t decide “I’d rather have a girlfriend than ever travel again. If it takes spending the summer in the woods, even though I’ll hate it, I’ll do it.” Eventually you’ll be unhappy to be stuck at home and she’ll be unhappy to be stuck with someone who hates camping. Keep going until you find someone whose tastes align with yours. I read recently that someone’s parent recommended looking for someone with similar interests, because when times are tough, it’s the shared interests that will keep you together. Every date is an opportunity to meet someone new and (hopefully) interesting. The bonus is if you find someone you’d like to see again, who’d also like to see you.

    1. anonymous says:

      Ha! Trollope! I LOVE Trollope! I’m about 3/4 of the way through his collected works (about 17,000 pages!).

      1. I just read (actually, listened to) my first Trollope (_The Warden_) about 2 months ago and I LOVED it. I can’t wait to get through the rest. I actually thought “How could I not have known how good this guy was?” My mom was a librarian, I was an English major, many of my friends are big readers, but no one ever said anything (that I can recall) about Trollope. I’m so excited to have found him.

    2. Not to be confused with “trollops”, right? *laugh*

  17. Geeze it sounds like I need a guy like you haha! Once girls grow up and realize that they have only been dating losers, they want nice guys! It sounds like you are doing everything right and just need to build up your confidence.

    Also, we all have baggage, but the trick is how we deal with it. Obviously you have dealt with yours very well. Listen to Wendy 100%

    Good Luck!

  18. everything wendy said, plus this: have you told your friends that you’re interested in dating? don’t limit yourself to match.com! tell your friends that when women ask about you, you’re definitely interested. it’s great to meet potential dates through your friends.

  19. Whatever you do LW, PLEASE do not ever develop the attitude that you will be forever alone. I know this is not the case now because you ARE going on dates and letting yourself out there – which is AWESOME. Yet please don’t be discouraged by the lack of second dates and give up entirely on the idea of companionship. Reading your letter sounds like a friend I have – except he’s totally resigned to be emotionally and physically alone now.

    I think you’re going towards a positive path in your personal life LW. Just remember while you’re dating to please keep an open-mind, eye and ear of your date and surroundings, develop a sense of wonder and curiosity no matter where you go, display a respectful and honorable demeanor to whoever you present yourself to and politely stand your ground on your convictions. Just doing that alone will make you an ideal date to most available women.

  20. My husband was a late bloomer. He didn’t have the difficult childhood you had, but was painfully shy – or so I’m told, he’s really come out of his shell and that was something he really worked on doing for himself. Kisses and more intimate relations came a lot later for him. But if they hadn’t we might never have been together (he’s several years older than me). He really is a great guy that has a lot to offer, and I think the extra time it took for him made him a better person in the long run.

  21. Everybody here gave wonderful advice. I’m throwing my 2cents in, from personal experience. Don’t be nervous about dates. Most likely, she’ll be just as nervous as you are, and it will be awkward and uncomfortable for both of you. Also, be yourself. Don’t try to put up an image of who you think she’d like. Nice, mature women (the kind you want to end up with) see right through BS. Also, it saves time for both of you, when she discovers you’re not exactly what she wants. Which, by the way, does not mean you should change anything about yourself. About this last bit, you can only hope that she’s being honest as well.

    I’m curious about how old are the girls you dated. You’re probably not going to have much luck with 22-23 years olds. Try to date women your age, or up to 2-3 years older than you. You’re way mature for your age, and more mature women will recognize and appreciate it.

    It’s been mentioned, but I’ll say it again – don’t make kissing/getting laid the purpose of dating, but rather getting to know someone. Lowering the stakes will make the experience of dating more enjoyable (at least for me). If she’s impatient and takes the initiative, go with the flow.

    Good luck!

  22. moonflowers says:

    First off, bravo to you for transcending a painful past and for taking such good care of your sister. You have no reason to feel at all embarrassed about your lack of experience in dating, because you’ve had to spend extra time to get your life in a good place. It’s a good and healthy sign that you’ve made sure to get your shit together, and women who are serious about you will appreciate that.

    Second, women who are really into you won’t care about lack of intimate experience. The only things she cares about are if you are respecting her personal boudaries (firm, serious “no”, drawing back, etc) and if she doesn’t get hurt. If you are following her feedback and being responsive to her physical and verbal cues, and start small and see where it goes, you will do just fine. Just don’t suck or lick her face or get slobber anywhere (not that I think you will, but it appears to be a common problem…).

    Third, as much as what you say on a date is important, it’s also important how you make her feel. People want to be around folks that make them feel good – relaxed, happy, safe. If you are nervous or uncomfortable, or aren’t giving her an out due to fear of rejection, she will end up feeling somewhat uneasy no matter what you say. On the other hand, if you can put her at ease and help her feel relaxed and respected (and thus safe) with you, she’ll be more inclined to want to be around you more, and paradoxically will even let you push those boudaries a bit more (ie more intimacy).

    Finally, I sometimes read the dating advice men have written for other men, and I can’t help but laugh at how overly complicated it is. All the “how to talk to girls” guides out there overlook the simple fact that women are people too, and want mostly the same things in relationship partners that men want – kindness, empathy, confidence, humor, intelligence, and having one’s shit together. There’s no rule as to what to say that doesn’t also apply in other situations like interviewing or any other scenario in which you want to leave a good impression.

    Good luck in your dating journey. 🙂 Don’t ever give up hope, and don’t take being single as a sign that something’s terribly wrong with you either. 🙂

  23. I remember my first kiss- a month after i turned 21. I was really nervous and it was not expected, and afterwards I was like wow… It’s a lot simpler then I even thought. I was always worried I would turn my head the wrong way or my lips wouldn’t be right, or just stupid little worries and I think thats why I held off until then, because although I had chances when I was 19-20, I was like they are going to think i’m an inexperienced girl who doesn’t know how to kiss so i delayed it and delayed it until I was finally like, I’m just gonna do it. And I have kissed a few guys in the year and a half since then (Seems the first of anything always takes the longest then they come in droves! First kiss, first boyfriend, first date, etc.) and my third kiss even told me I was a great kisser, so really it doesn’t take a lot of art or technique. Just have fun and enjoy it! You sound like a great guy, and I’m sure girls will pick up on that. Good luck! Just be confident and happy, and that will be a good start to making a girl comfortable:)

  24. Painted_lady says:

    LW, my best guy friend was in the same spot as you a year ago. He had never been kissed or gotten laid, and I’m not even sure he’d had a real date. He’s the same age as you, and about eight months ago, something clicked into place. He’s been on dates, made out with a bunch of people and finally, finally turned in the dreaded V-card. He’s in a relationship now, and a huge part of his recent success was that he finally relaxed a bit. I attribute a lot of that to a major health scare about a year ago – I think he finally owned both that life is short and that obviously getting a little rejection isn’t the worst thing that can happen. You’ve got both of those lessons under your belt; you went through terrible things and came out alive on the other side. You’ve been through enough to break a weaker person, and having contended with that with such grace and wisdom, use that same grace and wisdom to deal with the oposit sex who are far less traumatic to deal with in comparison.

    Here’s another thing: my boyfriend was in an abusive relationship throughout college and afterward. He only gives out this information to trusted friends, and for a long time he thought it made him “damaged goods.” For me, though, after he trusted me enough to give me all the details, it’s a source of comfort because I know his strength. I know that, in out lives together, the inevitable hurts and disappointments that can’t help but happen between two people no matter how much they love each other aren’t going to become too much for him. Any stress I – as his well-intended but occasional Type A neurotic mess of a girlfriend – will place on his shoulders will be something he can carry. And he does so with such strength and kindness that I’m occasionally shocked and simultaneously touched. You have this strength as well. Let it be your source of confidence, whenever you decide to relate your story to the women in your life, and once you have told them, know that your strength that stems from your past is by no means a liability.

    1. aw i really like this. its a great perspective of turning tragedy into greatness.

  25. LW, i think that everyone here has awesome, awesome advice for your situation. listen, take notes, impliment it, and bookmark this page and whenever you are feeling down or sad, or lonely, or whatever- come here and read all these things.

    i am a firm believer that there is someone out there for everyone. no one is destined to be alone, too “damaged” for anyone to want them, or too inexperienced. i just believe that there is no way that we are all on this earth doing whatever were doing, and meant to do it all by ourselves. there are seriously like 9 billion people on the earth or something crazy like that… you have tried to date 3 of them. there is so much more out there (in terms of the dating pool) that you dont even know exists yet- just start doing it, just start dating, meeting people, flirting, going out, whatever! just start, and something is bound to happen in your favor.

    oh, and trust me, the right girl is not going to care in the slightest that she will be your first kiss- she will probably be honored more then anything.

    1. Painted_lady says:

      Good points!!! Seriously, if I’d stopped at the third date I had where the guy didn’t want a second date, I’d have stopped dating at 16. I also noticed during my brief foray into the online dating world – I gave it up after a month – that there are fewer second dates there than people you meet face-to-face. I think it’s a combination of knowing there are a lot of other options out there and the lack of interaction prior to the date to let you know whether or not there’s chemistry. I was guilty of it, too. I knew there were other, better options out there, and I also found myself on dates with men whom I never would have dated if I met them for the first time at a party. I know a lot of the dates I had felt the same way. Not saying the LW should stop using Match, just that it’s one of the things to take into consideration.

  26. you sound desperate and uncomfortable.

    focus on your career, and your own life, and the rest will come together.
    or it won’t. there are no guarantees in life.I used to think like you, but not anymore…and I’m younger than you. My life is more important to me, than impressing some bimbo.

    If you want some practical advice, wait till you turn 30+. Then you will have the “power” so to speak.

  27. Wendy & a lot of people have offered up some great advice. Although you may already be doing this, I would also offer the idea of getting involved in activities where you could meet women outside of online dating (this could in addition to your current efforts at match.com). Not the bar scene, but activities like volunteering or hobbies with a group component (cooking courses? co-ed sports teams?), something where you could have the opportunity to interact with people (including prospective single women) on a repeated, regular basis. My thinking is that in situations like these, your niceness might become even more apparent and your shyness would perhaps matter less than in a first date type of situation since people could get to know you better. Also, especially with volunteering situations, I would think that any single women that you might interact with would probably highly appreciate the niceness in a guy. And, I can’t help thinking that you must be incredibly strong and resilient to have survived your childhood; although you are likely quite busy with your job & family (sister) responsibilities, I think you would be a tremendous role model and inspiration if you were to mentor/tutor underprivileged or troubled youth. That’s tangential to dating advice, but in general, I think you should be very proud that you were able survive such horrors and despite all that, manage to be successful enough to not only support yourself, but be able (and willing) to support your sister. Though disclosing your full history probably wouldn’t be a good idea on introductory dates (not really “light” conversation fodder), I would hope that whomever you eventually end up seeing on a longer term basis would come to realize all that you have overcome and respect you that much more for the strength of character that you must have. Pretty much, I don’t think your past is anything to be ashamed of, and instead, you should be very proud of being able to overcome such obstacles to become the man you are now. I hope that women you date would see things similarly.

  28. I love Wendy’s reply! It’s great advice…take it!

    I think one of the sexiest qualities a man can posses is Confidence!
    If you feel good about yourself and you believe in yourself and you know your worth, other people will pick up on that. It doesn’t matter how many women you may or may not have kissed. That won’t matter to the right girl if you are a genuine, kind, sincere, confident man!

    How do you become that? Keep doing what you’re doing…going on dates, meeting people, and enjoy yourself without putting too much pressure on yourself. And before you know it, you will click with the right person at the right time.

    Good luck!

  29. Awwwww…LW, I just want to give you a huge hug!!

    You sound like a great guy who has his act together moreso than many of the men out there. As another girl who loves nice guys, the fact that you cared for your sister tells me that you are appreciate your family and know how to put them first. The fact that you haven’t kissed anybody tells me that you haven’t just dated because everyone else is doing it in high school, you understood that you weren’t ready to take a leap. Honestly, that shows SO MUCH maturity.

    Personally, I didn’t have my first kiss until I was 21 and I was actually really glad that I waited that long. I thought that when I told my current boyfriend (who happens to be the lucky guy who was indeed my first kiss) that he would think I was crazy for not having kissed anyone prior to that. In fact, he thought I was joking when I told him and has always respected that decision. Many of my nice-guy-loving friends around my age are holding off on dating and/or kissing because they just haven’t found the right guy yet and they don’t just want to date just to date. I promise, you aren’t alone!!

    Good luck, LW! Stay true to yourself and the right person will come along. 🙂

  30. AndreaMarie says:

    It’s all about self-confidence. Women love a man that is secure. I think what might be preventing you from getting to that first date is that this Never-been-kissed gorilla is sitting right on your back and it shows. It might be that you are so stressed/nervous over being inexperienced that you may come off as insecure/nervous on the date and maybe even a little disengaged. You can’t be 100% in to moment, enjoying getting to know her and vis versa if part of your mind is engaged in the “omg I never kissed anyone” dialoge. Trust me, women pick up on these things. Maybe your dates mistook your edginess for disinterest. Whatever the case, forget about your inexperience. Be the self-confident secure man that a wonderful woman would want. You have so much to be proud of. On your next date just allow yourself to be involved, don’t worry about getting a next date. Ask her things about herself, her life, her goals, and share yours. Let her know the real you and all the wonderful things you have to offer, not your insecurities.

    And ps..don’t worry about the kiss. Me personally, I don’t kiss on the first date so a guy not going in for one would be no big deal.

    Good luck!

  31. Jess of CityGirlsWorld.com says:

    I love this reply from Wendy!

    I just want to embellish one part to help LW shift his thinking. LW, don’t forget that dating is a 2-way interview. Once you have established that list of the things that YOU have to offer someone, be sure to take the time to measure whether your date is worth of them. Many inexperienced daters focus too much on how their date views them. Don’t skip over the part where YOU evaluate her. And its ok for her to notice that. It shows her that you are a person of value who is not available to just any old body. Certainly, don’t grill the girl! But inquire about her and observe. She’ll pick up those cues.

  32. Three things:

    Don’t depend on online dating. Meet women (even for friendly conversation) in other settings – groups, clubs, classes, etc – places where conversation is easy to start. These places will increase your comfort level and you might even meet someone you click with.

    A secret: There are women out there who think an inexperienced guy is hot. Believe it or not. I once met a guy (a bit younger than me) who was totally inexperienced. It really turned me on to be his ‘first’ in everything!

    Confidence is not necessary for every woman. I happen to like a guy who is a bit insecure and does not know the real value of what he has to offer. Insecurity is different from desperation. Shyness and insecurity can be very attractive – especially in a guy who has a lot to offer in terms of his character and values – but may not be aware of his worth. Desperation is something different – it means chasing after women – any women – and is not attractive.

    So, rock your shyness, rock your insecurity, rock your inexperience. Don’t talk about them – no need to (unless it comes up naturally in a deeper-level conversation), just accept them as a part of who you are. Girls who will like you will like all of you.

  33. Temperance says:


    My FH did not kiss a girl until he was 21. (That would be me.) I know that you are somewhat older than that, but you don’t really owe your whole backstory up front to any girl that you meet.

    I am against online dating for someone that hasn’t dated in the past. Online dating is like a job interview; there’s no “meet cute”, there’s already some pressure upon the first meeting, you know? It might be better for you to try and meet women in real life so you can learn to talk to women rather than setting up dates first.

    You’re cute! You should have no problems once you get some practice in, I promise. I think letting girls know that you are shy up front can be endearing and charming … just don’t ever, ever, ever say that you’re not like those “other” nice guys. That just makes it seem like you are one. 🙂

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