“What are the Most Important Dating Rules?”

I’ve read a lot of information online, in books, and in magazines regarding sex, dating and relationships and I notice a huge problem. Everything is so conflictual and it’s all very confusing to me because I’m pretty new to dating (I started at 17 and now I’m 20). I’ve had plenty of flings but no long-term relationships as of yet. One website will tell me: “Do not chase a man; let him pursue you. If you chase him it will be the kiss of death to his attraction to you.” And another states: “Men actually like it when a woman makes the first move sometimes and does 50% of the pursuing from there on out. When men like a challenge they mean they like a woman who is independent, confident, assertive and who doesn’t need them but chooses to be with them.”

So I’m just sitting here thinking which do I do? What if one of them is wrong and I ruin a potentially good relationship? Another thing is the whole concept of virginity. I’m a virgin and some articles say that men like virgins, while another website says men will not go out with you if you’re a virgin after a certain point. So which is it? Am I screwed or blessed to be a virgin? I understand a few things that I know a good quality guy would want in a partner:

1) Confidence
2) Similarity in beliefs and intelligence
3) Kindness
4) Sexual Attractiveness (to the individual guy)

So in your expert advice, what is really the best way to approach sex, dating and relationships? I know that’s a hard question to answer and it depends on the person but I just want to get it right, finally. I feel like I keep screwing up in some way if I am unable to find a long term relationship partner. — Relationship Newbie

It may be a cliché, but the best answer to your question about how to date is to be yourself and follow your gut. You want a guy to like you for YOU not for some character you’ve created to snag him. Not only is it exhausting trying to be someone you aren’t or behaving a certain way just to land a guy, it’ll blow up in your face when you eventually let your guard down and the guy realizes you aren’t who he thought you were. So, seriously, screw all the games and the “rules” you read about in magazines and books and websites, and stick to the only rule that truly matters when it comes to dating: be yourself, even — nay, especially — if part of who you are is a virgin. The last thing you need to do is go out and have sex or lie about having had sex just so some dude will want to date you. Trust: you don’t want a guy who would rule you out because you’re a virgin. Nor would you want a guy who only likes you because you’re a virgin. Gross. So … be yourself, but show your different layers. Don’t let your sexual identity or your lack of dating experience be what you lead with.

Another mistake you need to avoid is coming on too strong. It’s okay to pursue a guy, but don’t chase him. This isn’t about “letting him chase you” or whatever inane nonsense you’ve read somewhere (dating isn’t a race, for Christ’s sake), but rather remaining enough of a challenge that the guy knows he has to put in some effort. Frankly, as important as it is to be confident, kind, and smart, it’s just as important to give a guy the chance to work for you. Why? Because it keeps him interested.

You know that game Crainium? Well, I played it with some friends for the first time on Thanksgiving and let me tell you something: I was bored. Like, really bored. The game was so easy, I had nothing to work for. I didn’t get that zing I feel when, say, I get the Final Jeopardy question right. In fact, I didn’t get a zing at all because the questions were all too easy and it took zero effort on my part to answer them correctly (plus, the bubbly had gone flat). That’s what happens when you make it too easy for a guy. There’s no zing and he gets bored. So, give him a little zing; keep your bubbly bubbly. If you ask him out for the first date, let him plan the second one. If you’ve told him two or three times how much you enjoy his company and he hasn’t said something similar to you, hold your tongue. Don’t share all your feelings for him right off that bat. Don’t hide them either, but don’t be an open book. Let him take time turning the pages and soaking up the story of who you are and how you two work together before giving him the whole plot.

Forget everything else you’ve read about dating and relating and remember these two tips: be yourself, and give him a little something to work for. Not much else matters too much — at least not anything you shouldn’t already be doing in life: dress appropriately; don’t eat with your mouth open; be safe; don’t talk too much about yourself; and pinch your cheeks for a pop of color.

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


  1. Remember, guys don’t get “hints”

    That’s mostly because hints are pretty much indistinguishable from random noise.

    1. For. Real. Say what you mean ladies. Or, if you insist on making us guess, how about not punishing us for not guessing the thing you knew you wanted all along. Also, you’ll always wonder if we really did know, and picked the wrong thing deliberately just to try and disincentivize the guessing game.

      1. lets_be_honest says:

        Or you could just take ALL the fun out of dating JD. Jeez.

      2. fast eddie says:

        I keep telling my wife that mind reading isn’t among my talents, but she has yet to hear me. Perhaps a hearing aid is required???

    2. Thank you for the first laugh out loud of the day!!!

      (I do agree with it, too.)

  2. My mom always gave me great advice to be yourself and just be nice (as in don’t play games). Remember, YOU only want to be in a relationship with someone who likes you for yourself. So that playing games and following rules thing can hide who you really are. Plus, if you don’t know how to date the best way is to get some more experience dating! If you screw it up (which you probably won’t) the worse thing can happen is that you date someone even better later on. This isn’t life or death, so please have some fun and don’t stress too much. And any guy that you are going to have a great relationship with won’t leave you because you didn’t follow some stupid dating rule.

    1. lets_be_honest says:

      Its so funny how we seem to only grasp that entirely once we are older. Could I mold myself into the perfect woman for a crush? Probably. Is that really what you want though?
      Loved all your advice.

    2. SpaceySteph says:

      Totally agree with your advice Kerry. The LW already seems like she’s taking it a little to seriously by doing all this reading up on it. Dating isn’t a test you can study for and then ace, its very subjective. Thats why all the advice is conflicting, people want different things.
      Be you, enjoy yourself, and if all else fails, pick “C,” 😉

    3. I wish all the guys I have dated were honest about who they really are from the get-go instead of trying to look “perfect” in the beginning. I would have dodged a lot more bullets before I got attached.

  3. Most guys your age aren’t going to have it all figured out either…and more of them than you think have little to no real sexual experience. So relax, have fun, and when something goofy happens, remember…if you are going to laugh about something later, you may as well laugh about it now.

    1. One more thing: “I feel like I keep screwing up in some way if I am unable to find a long term relationship partner.” No no no!! It’s a process…learn, have fun, it’s not a pass/fail!

  4. I totally agree with Wendy. Those books are basically saying that you should be in the middle. Not too forward and not a wallflower either I always had lots of dates and here is how. I had so much fun and I was super silly and loved my life. Also, you have to go out and do different things. If you go to the same place every weekend, then you see the same tired people. When guys were around I made eye contact and smiled. I was interested in what they had to say. It is better to be interested then interesting. So many girls seem snobby because they are too shy. Trust me, if you are nice to a guy, smile, and laugh, he will ask you out if he likes you. If he doesn’t, then just move on.

  5. Honey, you are WAAAAY overthinking this. I understand the notion that more information makes you feel like you’ll be better at dating when it happens, but you’re just in your own head too much. Food for thought: have you ever thought about walking up stairs? How each leg has to move so you can go up them? I don’t know about you, but sometimes, about 4 stairs up I overthink things and I suddenly feel like I’m going to fall on my face (maybe it’s just me). But when you don’t think about it at all, it’s no problem.

    If you were, say 42, and had been on hundreds of dates and dozens of relationships, I’d say you probably need to analyze your style. But you’re young! This is the time to figure out who you are and how you WANT to date, not how you should date. Just do it and learn what works best for you as you go.

    1. GatorGirl says:

      I’m glad I’m not the only one who was surprised at the tone of this letter given the LW’s age.

      LW, you’re 20. Relax, have fun and be yourself. There is no magic peice of advice that will land you a great relationship. It is going to take time and many dates. Chill out and go to places that interest you, take up a hobby, join a church (or the like) that will allow you to meet more people your own age. Be happy and healthy and a relationship will come.

    2. cookiesandcream says:

      I thought the same thing when I read the letter! LW, I hate to break it to you, but there are just some things you have to learn through experience. There are some things in life you can never be prepared for, no matter how many articles you read.

      haha, I liked your stair analogy because I have the same problem with going down stairs! I have a huge fear of heights, so whenever I look down the stairs I get a little dizzy because it seems like I’m so high up.

    3. See, I kind of disagree here. Think about being 20 and navigating dating. If you are looking around and seeing other girls get asked out and not you, you start to wonder what is going on. I am not saying that you shouldn’t be yourself but there is an art to dating and certain steps that are always taken. If you weren’t let in on the secret, then you are left on the sidelines feeling confused and alone.

      1. I’d agree with you if that was the situation that the LW was in. She said she’s been on dates, she just doesn’t know the proper “dating etiquette”. A magazine, an advice columnist, even her best friends probably can’t tell her if kissing a guy on the first date is the right move at the time. It depends on how she feels and the vibe from the guy. I think that’s what she has problems with: she doesn’t know her dating identity. And to expect to know that at 20 is crazy! It’ll take time and probably some failure to learn and that’s ok. She’s still young and bouncy and should be just fine trying it on her own.

  6. “what is really the best way to approach sex, dating and relationships?”

    Those are three very distinct things,no one piece of advice will cover them all – other than just being comfortable with yourself. Focus on dating first, the rest will fall in to place.

  7. My best dating advice: Stay the hell away from Cosmo magazine!!!!!!!!!!! Seriously.

    1. lets_be_honest says:

      What are you saying MissDre? Should I not have shaved a strawberry shape into my nether regions and dyed it red? Do you think he didn’t actually like my scrunchie around his you-know-what? Is this why I can’t hold down a relationship?

      1. No, you should have wrapped his testicles in plastic wrap and hummed on them! Then you would’ve kept him for sure!!

      2. Just be careful with the “step children”…..that’s all any man can ask.

    2. bahaha… “cosmo says the darndest things” on collegecandy is a funny column they do… so true.

      but seriously, cosmo really does suck

      1. My favourite is the Pervocracy’s Cosmocking! So funny.

  8. callmehobo says:

    Well, I think the first thing you should do is take a deeeeeeep breath.

    LW, just be yourself. I know that is so cliched, but seriously, don’t ever compromise yourself for a partner. It’s just a messy breakup waiting to happen.

    However, when you find someone that you really like, all this is going to be a little bit easier. Because right now, you are trying to theoretically date EVERY guy. But when you only have to think about one guy likes, thinks, prefers it’s not nearly as intimidating. Ok- it’s still a little a scary, but it’s totally worth it at that point 😀

  9. Skyblossom says:

    I think it comes down to being yourself, meaning do things you enjoy with people who also enjoy those things and you will meet people with similar interests. You won’t end up dating most of those people but you will develop some great friendships, male and female, and if and when the feelings are mutual, date someone who could become a serious partner. Putting the emphasis on fun, interesting, stimulating activities as your first priority will allow the rest to happen naturally.

  10. Wendy gave great advice, and there’s one thing I want to add– The objective of dating is to GET TO KNOW someone and then make the decision if you like them enough to keep going out with them. So many women (and men) think that somone liking them or lusting after them is the ultimate goal (shows like The Bachelor/Bachelorette glorify this and it drives me nuts!!), but really the goal is to find someone who YOU like and get along with, and hopefully they feel the same way you do. So if a guy likes you, that’s great, but make sure that you like him too.

  11. lets_be_honest says:

    Heyyy Addie Pray! Happy Belated Birthday 🙂

    1. Addie Pray says:

      Hey, thanks, lbh! You’re a sweet pea.

  12. Trying to think back 15 years ago when I started dating my husband in my late teens. What worked? He was much more grounded then I was, but I was transitioning quickly into with having direction. What we would later be termed as ‘having his sh!t together”. My apologies for the profanity. This is the same rule of thumb I use for selecting Godparents for my children.

    For instance at the time I avoided guys who didn’t go to class, had poor GPAs, or lacked a vocational skill/training. It wasn’t a direct question to my husband, but I learn this when a person is talking about what they do. Usually people who are actually doing something productive Monday through Friday talk about it, rather about what they do on the weekends.

    If a relationship starts in your late teens/early twenties, a couple has to start off on the same page in terms of maturity and grow at the same rate to make it work long term.

  13. Jess of CityGirlsWorld.com says:

    Another MAJOR theme in how to approach dating while being yourself is this:


    If and when you fall for someone, it can be really easy to get lost in them, be too generous, make it too easy for them, spill your heart out. Too much and too fast.

    As you navigate dating and love, stop periodically to ask yourself, “Am I acting with self-respect? Is this consistent with my values?”



    As you navigate dating and love, ALSO stop periodically to ask yourself, “Am I receiving the same amount of love/attention that I am giving?” When the throws of hormones have you in their grip, its hard to see clearly. Use mirroring to keep your actions in check so that you are not getting ahead of your partner. Similarly, seek balance with new love AND the other areas of your life. Make sure friends, family, work, and school still have a substantial place in your life after dating/love is added.

    1. GingerLaine says:

      If I could go back & tell my 18 year old self anything, it would be this. All of this.

      I thought that the way to get a guy’s attention was to BE the center of attention. Hm. Not so much. After so many failed crushes, FWBs, random hookups, I decided no more. I was not going to keep making my life a soap opera. I would not seek attention at all costs. I would not let someone let me do things for them, cater to them, drive to them, fawn all over them ANY MORE. I was going to be more & do more – not for other people this time, but for myself. Shortly after that, a good friend expressed interest in dating casually. I knew he was also dating other girls. I told him that as far as I was concerned, we were too close platonically to be casual romantically, and that when he was ready to be serious, I’d be around, but I wasn’t going to compete for him or be his fall-back girl. 10 years later, I’m married to him. 🙂

      The heartbreak I could have saved myself by just being me, honoring myself, and letting things just play out instead of forcing square pegs. This comment really resonated with me, Jess. It’s so true & the kind of lesson I wish someone had taught me long ago before I had to learn it the hard way. 🙂

      1. Jess of CityGirlsWorld.com says:

        Thanks Ginger! I’m so glad it resonated. I feel the same way as you. Like, in my 30s I needed the “open up” and “lighten up” type advice. But at age 20, I was more likely to make love the center of my universe and lose myself to it.

        Now, would I have listened to my 35 year old self when I was 20? That’s another story!

      2. Great advice Jess!

        But yeah, who knows if our younger selves would have taken it. But maybe that’s ok, maybe it’s ok to learn by failing. Look how enlightened you are now! 🙂

      3. Jess of CityGirlsWorld.com says:

        Thanks my dear!

  14. Awesome advice Wendy. Whether you’re 15, 25, 40, or any age, it’s great to remember that things will progress naturally and there’s no sense in forcing it.

    LW, I recently joined the dating game again. It’s been a while. I read the articles, I dated, and I freaked out so much about what I should, or should not do. I wasn’t myself and I couldn’t relax. Needless to say, things fizzled.

    The real, long-term relationships I’ve been in, there have been three, I never played the game. I was myself. And I was liked for being me. I need to remember that when I get back out there. I don’t know why I didn’t think it would work a fourth, or fifth or even sixth time.

  15. Loved Wendy’s advice.

    Let dating be FUN. I’m guessing your an analytical type who breaks everything down, LW. I can be that way too. But dating isn’t all about “getting it right”, it’s about enjoying the ride! You will make mistakes. There will be things you wish you could do over. There will at times be awkwardness. But those are things that you will remember with your girlfriends in 10 years and just laugh about! Being yourself is incredibly important when dating. If you put on a face and lie about who you are, you are lying both to him and to yourself. If you lie to yourself you won’t attract guys who are truly compatible with you.

    I have been dating my boyfriend for almost 2 1/2 years. Right away when they met him, my friends told me how glad they are that I’m still the same person, just now I’m in a relationship. Always ALWAYS be true to yourself. The guy for you will love you for YOU.

  16. ReadingIsFundamental says:

    There are two things you need to know:

    (1) Men are people, just like women. Strange as it may seem, we’re all different. What drives one man wild may make another man say “Um, no.”. Some men will like you, and some won’t.

    (2) You need to be yourself. That doesn’t mean that you don’t need to learn and grow as you gain experience in life. It means that if you decide that you need to pretend to be someone you’re not just to “get a man”, you’re going to wind up being very very unhappy when you’re 40.

  17. Will.i.am says:

    Dating can be so much fun. I’ve even went out on dates with women I wasn’t that interested in to see if there was something I was overlooking. Most of the time it wasn’t, but it allows me to gather more of what I would want and not want in a relationship. As humans, we evolve, and our interest change, so I’m always up to trying something new. Even if I find out I don’t like it, you never would have known if you didn’t try it. There’s some things I just won’t try, but I also know I would never be interested in someone who does those things.

    Like other posters have said, dating is all about being yourself. If you have a personality and like to make people laugh, let that personality out. Don’t go and be someone that you aren’t on a date just so you can get (or keep) a mate. I’m a smartass at times and I like the sound of my own voice a little too much at times, but it is who I am. I will never stop being that type of person, because that is what makes me interesting, but I’m not going to be the smartass/know it all in every group setting. Those are my two querks that I try harder to keep in check, because I know that both are clearly turnoffs to the opposite sex.

    1. See, I totally agree. It is be yourself but be the best possible version of yourself. When you are at the bar, you shouldn’t unload all your drama and wierd quirks. Dating is for letting quirks out. Good example: My husband is an avid Professional Wrestling fan. If he had led with that, I don’t know if I would have said yes to the first date. I found that out naturally over time and it is fine.

  18. Painted_lady says:

    Here’s a big one I finally decided awhile back: if there’s dating advice that makes you feel inadequate, panicked, or like you’re going to be alone forever, DON’T TAKE IT. Seriously, there are certain advice formats (ahem, Cosmo) whose entire purpose seems to be to convince you that you’re doing everything wrong. Don’t buy it. You’re fine like you are.

  19. ele4phant says:

    Not having a relationship by the age of 20 is not that unusual. It may feel like you’ve been dating forever, but you’ve only been in the game three years. It may seem like you should have had a boyfriend by now, but the fact you haven’t had one yet doesn’t mean you’re destined to end up an old maid.

    Be confident, be friendly, be open to things, and relax. If you can do that, you’ll find a boyfriend when its right.

    1. SpaceySteph says:

      Definitely. At 20 I hadn’t even had a fling. I was a never been kissed virgin until I was well into 21 and halfway through my senior year in college. Since then I’ve had 2 long term boyfriends, and a couple dating site flings. You’re doing just fine!

      1. ele4phant says:

        Me too. While I thought I had had a serious relationships in high school, in retrospect despite the intensity of my feelings, a three month relationship does not count as long-term or serious in any one else’s book.

        I didn’t have a real, long term adult relationship until I was twenty (I had started dating at 15, so I had a few more years on the LW despite being the same age she is now). Now I am several years into my second serious relationship.

        Many of my friends didn’t get into relationships until their early twenties, (one of them was twenty-five when she first got kissed, lost her virginity, and started a serious relationship. She never felt weird about it, she was just waiting for a guy worth her time).

        As long as the LW doesn’t freak out about never having a boyfriend, she’ll be fine. She’s in plenty of good company, and it will happen when its supposed to happen.

  20. Don’t play hard to get, BE hard to get. Have a really cool life going on on the side and work on that part before even attempting something with any guy.
    Because if it’s only a lie you’re going to stop faking eventually, and it’s going to be a mess. You’re going to realize you allowed yourself to get attached to someone who was in it for the thrill of the competition and who is now just sitting there scratching his balls and not doing an effort, and you don’t want that. You want to know from the beginning what exactly he wants to give you and your real life, and not trick him with mirrors and glitter into doing his best just for a while until he has you all for himself (and discovers that those times you declined his invitations to go hang out with your magical bunch of PhD holding pornostar friends who are all also heirs you were actually just sitting at home watching TV).

    1. ahhh mirrors & glitter : ) thank goodness! that is actually one of my favorite parts of being a woman & dating men…. is the shiny things men do to look special while trying to mate! Those dear, dear peacocks…

      lw, dating is fun! no worries, just keep breathing & when you’re sitting at home & you’re like, “I know I shouldn’t call him (for whatever reason)… but I really kind of feel like I have to” – save yourself time & energy & just DO NOT do it. Not only will it take the “zing” out of the game, but if he really never does call you again (horrors, lol), then it saves you a ton of time & energy worrying about him.

      ALSO & finally – you can date a bunch of people at once without getting serious about 1 guy – then you will feel calm & you can let him “lead” the relationship dance, which makes your job very easy & don’t be alarmed if he lets another young man “cut in” haha – just smile, say thank you, then smile at the next one : )

  21. Honey – as “new” to relationships and dating as you are, it’s okay to “not get it” yet. It’s a learning process. Ongoing, for life. Trust me. Even after being married twice, with four kids – I’m still learning. Every relationship, I learn something new, or relearn something. Every person (guys and gals) is different, therefore every relationship will be different, and you should not judge each new one based on the merits of the last.

    When going on a “first date”, don’t think of it as potentially being a make-or-break thing. This isn’t your “ever after romance”, but a chance at a new friend. Seriously, as long as you don’t take the date too seriously, you will be calm enough to let your personality shine. It also conveys that you aren’t clingy and desperate, and willing to allow others their chance to talk and have fun. Bonus – if you and the date don’t work out, you may very well end up with a really good friend who can set you up with Mr. Right (for the time being).

    You say you’ve had some flings. If you are looking for a relationship and not random/casual sexual encounters, then you need to stop having random/sexual encounters with first/second dates when you don’t think there’s going to be an actual relationship. Guys talk. Rumors get out that you’ll “put out” for a reasonably-priced dinner and a movie and sure, you’ll have plenty of first dates, but no real relationships. I’m not saying this to shame you, but to help you out. My half-sister (11 months younger than I am) thought that she needed to be exactly like me, and to do that, she thought she needed to sleep with every guy I did, date every guy I did, but she couldn’t figure out which was which, so she ended up screwing up a lot of things in high school. Especially when she found out that I’d only slept with one of the guys (a boyfriend) and had beaten the other 3 at a game of strip poker rather than the “save face” story they later told that she believed.

    Stop reading the magazines. They don’t care about YOU the individual, just the money you bring by purchasing their rag.

    1. Will.i.am says:

      That’s something I will never understand. I’ve never been the type to talk about my sexual endeavors. It’s not anyone’s business but mine and the person I slept with. To me, that is classless.

      I don’t want anyone to be type cast into people thinking that they are “easy” because they heard from Tom’s brother, sisters, cousin Tracy. I’ve had to have that talk in the past, because they thought they could go tell the whole world what happened with us the night before. Sorry, I’m just not ok with that.

      1. You’re thinking with an adult brain. We’re talking idiot teenage boys who had access to money, who had parents that bought them new pick-up trucks or SUVs as soon as they turned 16 (if not sooner), and felt they had something to prove because they KNEW they were living off of Daddy’s money.

        I hear things are better in the schools now, but I really do have to wonder. We have more of a gang presence in more schools than we did 12-15 years ago, and now that weapons are banned, more handguns.

  22. ummmmm cranium owns actually, maybe you weren’t very good at it? sour grapes sort of sitch?

    1. No sour grapes! I got every answer right and won the game.

      1. ele4phant says:

        I hate the game too, but then again I’m not really a board game person.

      2. That’s how I feel about Catchphrase. I’m so good it’s almost boring!

      3. I feel that way about Apples to Apples. People are obsessed, but I find it stupid and way overly simplistic. I think a lot of people confuse a game being EASY with a game being FUN. I’m a total game snob!

      4. lets_be_honest says:

        I really am hoping some commenter replies to this complaining about how hard Apples to Apples was for them to win and how you killed their pride built only this one-time-Apples-win achievement.

      5. ele4phant says:

        Oh I love apples to apples! Mostly because its not really a board game at all, each just gets people to talk and joke around.

      6. Ooh, but Apples to Apples IS fun!

    2. I know, that made me sad too. I adore cranium! But Wendy’s comment about it being insultingly easy makes me feel a little ashamed. Oh well, to each his/her own, right?

      1. I love Cranium, but you have to be drunk. Then its harder. And rude things get made out of the clay. And you have to be in a bach, on holiday in the pouring rain, with nothing else to do.

  23. I really liked how Wendy differentiated between forcing guys to CHASE you and simply remaining a challenge. Holding back some when you first meet someone, and expecting *at least* reciprocal levels of initiating hanging out and compliments and effort in general, is such a fundamentally important part of social intelligence. (And it doesn’t just apply to romantic interests, but also to new friendships or even business contacts.)

    I always cringe when I hear people say things like “well I’m going to be myself no matter what so I’m going to tell him everything bad about myself on the first date and if he doesn’t like it fuck him!” I guess that works for some, but I think that mentally and emotionally healthy people need to let new connections breath and develop organically. You shouldn’t be dishonest or hide who you are, but I like to think about it in terms of earning being in your life. People show who they are through their actions over time. You are a prize that anyone would be lucky to have in their life, so let them show you through their actions that they are deserving of your trust and time.

    I’m kind of just going off on a tangent now, but I have a lot of dating experience and I think I learned a lot that seemed to work well for me! I liked Wendy’s response because it struck a balance between being honest and giving *too much* of yourself before it’s warranted. I think that is the main thing people struggle with in dating, and honestly I think it’s something that most people have to practice at. So don’t kick yourself too much when you get rejected or find that you don’t like someone as much as you originally though. Dating is for the tough, and it can teach you some amazing things about yourself and human nature if you let it.

    I’ll close my rambling post by seconding Wendy’s suggestion to trust your gut. LW, you shouldn’t be so caught up in other people’s advice from all over the internet. You end up exactly where you have- confused and stuck between a bunch of contradictions from people that are probably just as clueless as you. Dating is not a science and there is no magic answer. Accept that, learn to be critical of the advice you get, and make decisions based on what you truly believe. This is YOUR life. Trust me, going with your gut and falling on your face feels infinitely better than blindly listening to some other person’s random advice (that you might not even agree with) and falling on your face. At least when you make your own mistakes, you learn something real. Your gut is probably smarter than you think.

    1. yes. agree. you shouldn’t lie and say your wife died instead of saying you are divorced..

      1. Lol

  24. LW,

    One thing not stressed enough in the comments that I’ve read is you need to know what you are looking for in a partner too. From the sounds of it…you just want a relationship…don’t forget what you need too and be ready to hold out / move on to the next guy if someone isn’t meeting what you want either…it is a two way street.

    No one directly approached the virigin comment either. There is no rule when it comes to anything like this in dating. Some guys would “kill” for a girl without a history – other guys may think you are a prude. The important thing is to understand why you are still a virgin (waiting for marriage, the right guy, whatever) and make sure that whoever you choose to date has a similar feeling or can respect how you feel about it. This advice goes for a lot of other things too…be you, be comfortable in you, and don’t sacrifice parts of yourself for someone else.

    And always remember being single is way better than being in a bad relationship.

  25. spanishdoll says:

    One important thing to remember is that very few people are naturally good at dating. The people that are super smooth with the opposite sex have probably gotten to that point by failing dozens of times. It’s all trial and error, and learning to be completely comfortable in your own skin no matter what kind of person is sitting across from you at the dinner table. The more opportunities you take to date, the quicker you’ll figure out what works for you.

    I would also like to reiterate what a few commenters have said before me…enjoy yourself and your own hobbies, and it will be much easier to make your dating life fall into place. I’ve been through quite a few cycles of being single, and found that the second I said “fuck dating! I’d rather be super cool in my own right,” my next boyfriend just wanders into my life. Active, passionate and confident people are irresistible!

  26. atraditionalist says:

    I’m like you LW. And I think you should listen to Carolynasaurus. Everything she said is bang on. I too have no idea what to do when dating. I constantly question myself, I don’t know my “dating identity”. I doubt guys’ feelings for me. I have tons of dating books and have been reading them for years-and guess what? I still have doubts! All the time. The only part of me that I do know is that I’m not one of those laid back, calm people (pointing out the obvious). But I think you (and me) need to JUST RELAX. I’m dating someone now and I tell myself that everyday. Concentrate on whether or not YOU like someone and scale back on focusing on whether they like you. At least that is starting to calm me down lol

  27. LW, you could literally take all the advice that you have ever read, somehow formulate “rules” through all the confusion and contradictions, and that still would not garauntee you anything- relationship, fling, whatever.

    dating isn’t science. its not cut and dry like data and statistics or something. its human beings trying to get to know each other and themselves and their lives to ultimately find happiness in some balanace of all those variables. every person is different, each “dream” life is different, and everyone’s definition of happiness is different, so really you have like 3 or 4 different variables that are going to be wildly different from each other everytime to try to put them together.

    what im trying to say is that you are not going to have a successful dating experience by trying to “play the game” correctly or “formulate” things correctly… its just not the way it works.

    my best advice? be friends with guys. dont find out on the first date about his family and his dog or whatever- get to know guys as friends first, and then let things progress organically that way. my boyfriend now was the first guy i was friends with before we dated, and it has been the best dating experience ever, because i already knew him.

    1. oh, and about the virginity thing… no respectable guy should care either way. that should not be either a deterrant or a bargaining chip. the right guy wont care.

  28. I just have one thing to say about the myth that you must wait for the man to pursue you or he won’t be interested: BULLSHIT. That may be the case with some men who prioritize their ego over any other person in the world, but not for real men. When I was 19, I struggled with that as well because I had a really cute coworker that I really wanted to go out with but he didn’t seem to notice me as I did him. After a month or two of trying to talk to him whenever possible and hoping we worked the same shifts, I just took the bull by the horns and asked him out. He said yes, and guess what? 8 years later we are still together and live together. Best decision I ever made. Turns out he’s the most down to earth guy I’ve ever met and too shy to ask a girl out.

  29. David Woods says:

    Dear Wendy, I agree with this information sooo much. As a person girl or boy, you need to VALUE oneself and know that ou are worth more than just sex or money, before you know how can i save my relationship you need to have one first, this comes with respect and trust in each other.

  30. I think it’s also worth mentioning that when someone really likes you and wants to be with you, you can’t really ‘mess things up’ or do anything wrong. (Within reason of course).
    You can’t be afraid of doing the wrong thing to drive him away. Everybody makes mistakes so if you’re so worried of doing or saying the wrong thing, then you’ll stop acting like yourself, and as everyone keeps saying…you really just need to be yourself.
    If you feel good about yourself and who you are, then you’ll attract someone who likes you for you, and you won’t need to act a certain way or be afraid of doing the wrong thing.

  31. fast eddie says:

    Reflecting on whom pursues whom, when she was 20 my goddaughter chased the man she married unashamedly 16 years ago. They’re very happy and have 2 wonderful little girls for me to spoil, I’m very grateful.

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