I Am a Nice Guy With Little Dating Experience. How Do I Get a Woman to Go Out With Me?


Good Morning Evan,

I have a bit of a dilemma. I am almost 21 years old and I have only dated one woman in my life and I dated her for 4 years. She broke up with me in the summer of 2006. I’ve asked out several women since then, and they all rejected me. Just a few months ago I moved to Florida, and I’ve asked out two women and they both said no to me, too. I think I must be cursed. I feel scared to ask out any other women for fear of being rejected. The worst thing about this is that the last woman told me to never change who I am because I gave her a rose for New Year’s Eve. She said a man had not done that for her in a long time. But if she won’t go out with me, how can I be myself? In a way, I have an identity and a dating crisis.

I heard you were an expert, so how do I get a woman to go out with me?


Nice guys rarely do well with women, but it’s not BECAUSE they’re nice. It’s because they have no confidence.

Dear Alex,

Your crisis isn’t an identity crisis or dating crisis; it’s a confidence and perception crisis.

Your sample size of experience is so small that you’ve turned every tiny setback into a disproportionately large failure. This is impacting your perception of the world to view yourself through a prism in which you are “cursed”, “scared”, “rejected” and afraid all in one paragraph.

So let’s shake you out of this funk and set your record straight.

(This goes for any other reader – male or female – who has ever felt a lack of confidence in his/her ability to date. Dating failures are almost ALWAYS perception and confidence problems and not real problems.)

Okay, Alex. Your question says it all: “How do I get a woman to go out with me?”

The answer is: “You don’t. You become the man that she wants to go out with.”

It may sound like wordplay, but I assure you, it’s not. Our job as human beings is not to make anybody do anything. Every email I receive that says, “How do I make a man want to commit to me?” misses the point. You can’t make a man do anything. All you can do is be the kind of woman that makes a man never want to never leave. The focus is on who you are, not on how you want him to act.

Same for you, my rose-giving friend.

You’re a nice guy. Nice guys rarely do well with women, but it’s not BECAUSE they’re nice. It’s because they have no confidence. They don’t inspire, they ask permission. They don’t lead, they follow. They don’t trust their judgment, they want to see if their judgment is okay with their girlfriend. And they certainly don’t believe that they’re good enough to get any woman interested in them – they just feel fortunate to be in the conversation at all. In short, nice guys have to grow a set of balls.

This isn’t my opinion. This is me, as a dating coach, translating what I’ve heard from thousands of women. They don’t like bad boys BECAUSE they treat them poorly – they like them IN SPITE of it. Why? Because bad boys inspire, excite, lead and generally appear to have things all under control.

Seriously, bro, you’ve asked out TWO women in Florida who weren’t interested – and now you’re afraid you’re cursed?

Women want to be equals with men; they don’t want to be able to control us. The second they can control you, Alex, they’ve lost all respect for you.

I’m guessing that you’re sending out a pretty strong signal to women that they can control you. This is something that feeds on itself and has led you to this crisis of confidence. Seriously, bro, you’ve asked out TWO women in Florida who weren’t interested – and now you’re afraid you’re cursed?

By extension, a baseball player who hasn’t gotten a hit in his first two at-bats must fear he’ll never get a hit again. An oncologist who has lost two patients to cancer must consider hanging up his scrubs. And someone who is unemployed and sent out two resumes without a response should pretty much resign himself to a lifetime of unemployment.

This is what I mean by your lack of perspective.

I’m not making fun of you – not at all! I’m a guy who had to ask out three people before he got a prom date; a guy who didn’t lose his virginity until his sophomore year in college; a guy who didn’t have a relationship over a year until he got married. This stuff doesn’t come naturally to lots of folks, which is precisely why I still have a job. And I am living proof that you can learn – with considerable practice – how to understand the opposite sex. Your problem is that you are more focused on having the opposite sex understand you.

This is very common (especially for women, who should reread that last sentence.)

Instead of hoping that the opposite sex suddenly starts appreciating you, your focus should be on understanding what the opposite sex finds attractive and making small steps to becoming that person.

A nice guy can still be nice and do well with women.

A strong woman can still be strong and do well with men.

But something fundamentally has to change in your attitude, Alex, in order to make a breakthrough.

For the sake of brevity, I’d recommend three things:

1) Drop the idea that you’re a failure. Nobody wants to buy a car from a salesman who doesn’t believe in his own product. Your insecurity and negativity and fear is all over you.

2) Find a few guy friends who are good with women. Hang around them. Take mental notes. I remember the first time I did this and realized that my friend – the rush chair of his fraternity – was so great with girls simply because he didn’t hit on any of them. He was like the mayor of the party – getting everyone drinks, dancing with everyone, making everyone laugh. He was so NOT concerned with what anyone thought because it was HIS place; he could do no wrong. Make the world your place, Alex, and women are going to want to hang out there.

3) Get used to failure. Thomas Edison tried 10,000 different ways before inventing the light bulb. Maybe he should have just stopped at 2 because he was “cursed”. Every successful person has failed at something. Most of us have failed a lot more than that.

And if you’re reading this and saying to yourself, “This makes sense, but HOW do I make these changes to develop more confidence and perspective?”, click here to learn more about my coaching. You’re probably a lot closer to success than you even realize. You just need a little push.

Good luck.

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  1. 22

    I also liked Lance’s suggestions of talking to as many people as you can, without an agenda. It’s a great way to get over shyness and develop social confidence. And confidence is what both men and women find attractive in potential dates.

    I also liked Jonsie’s suggestion of inviting women out as friends. When I was young I felt more comfortable going on dates that involved a group of people at first vs. the one on one type (eg; dinner/movie). The advantage of this is that it gives you and your date the opportunity to talk with others if you’re nervous or worry you will run out of things to talk about with each other.

  2. 23

    mic #18

    I’ve used the “I’ve got a boyfriend” technique before. Effective and requires no further explanation as to “why” you are not interested making it more awkward for both parties. Only useful though if it’s unlikely the guy will find out that you don’t actually have a boyfriend and catch you out for the liar you are lol!

    I was having a drink with a girl friend once when a guy came up and started hitting on her. She looked straight at him and said bluntly, “I’m not interested.” He looked a little sheepish, said “ok” and shuffled away. I looked at her and said, “Wow. That was direct, I just would have told the guy I had boyfriend.”

    She said, “I have my big girl pants on today. Though I did consider telling him I was gay.” (She isn’t) Then she said, “Oops!” and smiled.
    The guy sitting behind me had overheard her remark and was laughing. We started talking to him and he and I ended up dating.

    Generally though, I think more subtle cues are avoiding eye contact, turning away to engage someone else in conversation, or sometimes simply saying “I’m not in the market right now.”

    I feel for guys having to take most of the risk of rejection, but if you are a “nice girl” you don’t want to hurt the guy’s feelings if you aren’t interested by saying something that could come across as rude. Hence the popularity of the I-have-a-boyfriend blow off.

  3. 24

    “I Am a Nice Guy With Little Dating Experience. How Do I Get a Woman to Go Out With Me?”

    Don’t sweat it now, at age 21. Focus on school. Get a good career from school. Have a balanced life with friends, hobbies interests. Be physically fit and healthy.

    Don’t worry – you do those things. They’ll find you. Then you can weed them out.

  4. 25

    Karl is good-looking and has skills, it seems. Thanks for the particulars.

    Avoidance of eye contact isn’t always a sign of disinterest, though. Shy women just don’t make much eye contact. But that goes back to the idea of why some women complain about being approached by the wrong guys.

  5. 26

    what are the specific tricks women consciously use to quickly discourage romantic interest in undesirable (probably physically so) males?

    The most common one is that they will avoid eye contact to discourage the man from coming up and initiating a conversation in the first place.”

    I have REALLY got to work on this- I do a lot of breaking eye contact with men I’m interested in- only because I’m so nervous. So, if the woman’s anything like me, it’s not that she’s not interested, but she may be breaking eye contact because she’s nervous or doesn’t want to seem desperate. I know this probably doesn’t make the guys feel that much better, but just wanted to give my input.

  6. 27

    Also, why doesnt anyone write advice for women in how to get asked out by men she actually wants to go out with?
    The easiest way for women to be asked out by men they actually want to go out with is…..

    ….to ask out men that they actually want to go out with.

  7. 28
    Karl R

    A-L asked: (#20)
    “What percentage of women have you been interested in getting to know better but you picked up the cues from them that they weren’t interested?”

    I couldn’t begin to tell you. It’s normal for me to do what Lance (#4) suggested: “Talk to 100’s, even 1000’s, of women with no agenda and no interest whatsoever in the outcome.”

    Through dancing I’ve met at least a few hundred women. Through yoga, a few dozen. At church, dozens more. Many of these women are unavailable (married or otherwise taken), too old, too young, not what I’m looking for, etc. If I’m asking a woman to dance, my “agenda” is getting a dance partner for the next 3-6 minutes.

    I will try to figure out whether a woman is what I’m interested in, and whether she’s interested in me. But it’s a lot more important for me to remember the former than the latter. Her interest in me can change.

    mic said: (#25)
    “Karl is good-looking and has skills, it seems.”

    I’m some women’s type. I’m tall, thin, fit and pale; I wear glasses, have a baby face and a slightly receded hairline. If a woman wants the “manly man” look, she’ll have to go elsewhere.

    But I don’t have to be Hugh Jackman. If 1 woman in 5 finds me attractive (or 1 in 10, or 1 in 20), that’s sufficient.

    The main skill that I learned over the last few years (which has made a world of difference) was how to play to my strengths.

    mic said: (#25)
    “Shy women just don’t make much eye contact.”

    There’s a difference, but it’s hard to explain.

  8. 29

    You know, Twitter might do Alex some good. The same rules apply there as in the dating world! If you aren’t participating as a thoughtful community member, and simply try to push your agenda – you’ll be rejected (people won’t follow). You’ll learn timing – the art of when and how to bring up your agenda. You’ll get feedback on your approach – are followers increasing or decreasing. You can work on your approach – almost like a science experiment – Twitter provides volume (so your sample size will be large).

    Just a thought!

  9. 30

    Karl, your “world of difference” – how much more success with women (numbers, please) with presumably little change in appearance? Also, because appearance’s importance probably varies according to age, you and the women in question are how old?

    Concerning eye contact – looking away and looking back is more likely shyness than disinterest. Whether it’s done with a frown or not probably means a lot.

    Also, “I have a boyfriend” is not appreciated by men. “Then why are you here in this place without him?” Surely there is a better method. Even a sweet-sounding “Thanks, but no” might be better.

  10. 32

    Re: #30

    What would be the preferred method of rejection? Guys?

  11. 33
    Karl R

    mic asked: (#30)
    “Karl, your world of difference – how much more success with women (numbers, please)”

    I’ll break this down into the past 3 years, and the previous 10 years. During the previous 10 years, I had two exclusive relationships (5 and 6 months long). I had 1 or 2 dates with other women (maybe 10 women total, possibly fewer). I was basically waiting for relationships to “just happen”. That’s about as successful waiting for a good job to “just happen”.

    In the past 3 years I’ve had two relationships that were longer than six months. I’ve had 4 more that lasted 1-5 months. And there were at least a dozen ladies that I went on 1-3 dates with.

    “with presumably little change in appearance?”

    There’s been very little change during that time. Admittedly, that’s a strong advantage to me. Many of my peers are getting flabby, bald and wrinkled.

    You don’t need to take my word about my appearance. My profile on match.com is currently visible. Just do a search for Yoga_Class_Clown.

    “because appearance’s importance probably varies according to age, you and the women in question are how old?”

    I’m 39. The women (in the last 3 years) have ranged from 11 years younger to 9 years older. The oldest lady (48) may have been the most picky about appearance; she was certainly the most vocal about it. In her words: “I put a lot of effort into staying in shape. I expect my dates to also.”

    Selena asked: (#32)
    “What would be the preferred method of rejection?”

    Anything that’s polite and honest.
    Example: “I’m sorry, but I’m not interested.”

  12. 34

    What would be the preferred method of rejection? Guys?
    We will tell you as soon as one of you people ask one of us out.

  13. 35

    Hence, the prevalence of many older, single women today in this era where cheating the clock is much easier. There don’t seem to be many older, heterosexual men who make that level of effort – and hair loss seems to sabotage all else. Thanks for the detailed reply.

  14. 36
    David Gideon

    Alex, these four things will move you in the right direction…

    1. Purpose:

    Discover what your purpose is in life is and start pursuing it. Women like a man with clarity, goals, and who has his life together.

    2.Be social

    Start interacting with EVERYONE who crosses your path. You might be coming across as nervous or awkward when you approach women so the only way to overcome it is to practice your social skills until you get comfortable meeting new people.

    3.Be persistent.

    Don’t give up just because a girl isn’t showing interest initially or because the last girl said no. Keep approaching the girls you want to meet and displaying your personality until they see something they like.

    4.Stay positive

    Just being positive can turn many situations around. That means not getting mad at girls or getting all dejected when things don’t go as planned. Correct course and keep sailing with a smile on your face.

    David Gideon

    David Gideon´s last blog post…Mystery Method Documentary

  15. 37

    I would guess that you are asking for too big a commitment (a date) too fast. This discussion applies to American women only (sorry it’s so long):

    1. Fact: Women are conditioned to say “no.” From the time we are old enough to understand that boys and girls are different, everyone in society is telling us that “Men only want one thing” and it is our job as ‘good girls’ to make sure they don’t get it. So, the first rule is not to take “no” personally. It’s a knee-jerk reaction, not necessarily her. And the mere fact that she’s aware she’s conditioned (which most of them don’t) won’t stop it from happening.

    1a. If you want a woman to say “yes,” you have to get past fact number one. You do this by making it simple (or simpler) to say “yes.” Now, this doesn’t mean set her up to give a yes answer, because she’s had experience dodging that since high school, and it marks you as an amateur.

    1b. Phrasing is important. A woman will not say yes if you ask in a self-effacing way. NEVER make it easier to say no, because she’s already conditioned. “You wouldn’t want to go out on a date with me, would you?” is SURE to get you a turn down. Instead, say, “I am [activity] at [place] on [day] [morning/afternoon/evening]. Would you [like to] come with me?” So: “I am going hiking at the park on Saturday afternoon. Would you like to come with me?” It’s clear, it’s to the point, it’s specific, it shows planning, it’s non-threatening (it’s not dinner), and (theoretically) it’s something she’d like to do (see below).

    1c. A woman will say yes to smaller things rather than big things. So when speaking to women you’ve never met (say, at a bar or shopping center) don’t make it your aim to get a date, make it your aim to get her email addy (if young) or phone number (if older). Or make it your aim to find out when she will next be at that location, or if she’s going to see a certain band on Friday and make arrangments to “meet up.” This is NOT a date, it’s a non-threatening way for her to size you up.

    2. Which leads us to fact two: The greatest fear that women have, by far, is that they will be killed or hurt by a man. And when women are hurt or killed, more than 2/3s of the time it is by a male they know intimately or who wants to be intimate with them. By comparison, the greatest fear a man has is that he will be laughed at by a woman. Hmmmm.

    2a. Keeping your aim in mind, which is getting the woman to say yes, you need to reduce this fear of danger to a reasonable level. Strangers are scary. We learn that in kindergarten. A few pointers: don’t EVER loom over a woman. Particularly small ones. You will not come across as warm and cuddly, but threatening. Stay out of the personal space of women you don’t know well. Never try to break the touch barrier on first acquaintance, beyond a handshake if offered. If there is a woman you particularly want to meet, an introduction helps, especially if she is older.

    2b. Familiarity breeds comfort, and comfort is more likely to lead to a “yes.” But not too much familiarity, as that tends to lead to a younger woman seeing you as a “friend” which is not going to get you a date. With older women, particularly much older women, if you want to date them, you will probably have to get past the idea that you are too young for them, which requires more familiarity first. You probably should break the touch barrier with an older woman *before* you ask her out, but I’m thinking that’s still 4 weeks work unless you know she goes out with men your age. It should go without saying that stalking is a huge no-no.

    2c. Show concern for her safety. ALWAYS walk her to her car if it’s dark. If you take her home for any reason (even non-date related), ALWAYS walk her to her door. (which is not to say you get a good night kiss). Don’t overdo this or make a big deal of it. If she says, “You don’t have to do that.” reply with “My mother would kill me if I let you walk to your car alone.” or “If my father ever found out I didn’t see a woman all the way to her door, he’d disown me.” Make it about manners, not “the weakness of women.”

    3. Fact three: appearance matters. Yes it does. Anyone who says different lies or is ignorant to point of disbelief. Appearance always matters. Women are, like men, attracted to certain “types” and if you aren’t that type, you’re going to have difficulty. However, on acquaintance, that difficulty can be overcome, sometimes.

    3a. The corrollary to this is, appearance isn’t all about “physical looks”, at least with women. Women are interested in cleanliness, smell, put-together-ness, carriage, etc., more than men. Men are more about breasts and legs, women are much more concerned about hygiene. Really, if under your nails is dirty, where have you been? Don’t even think about touching me. Get over it and get with it.

    4. This is a point, not a fact. Women are entitled to know they are on a date. Don’t try to trap them by, for example, saying “A group of us are going to eat steak on Friday night” and then it turns out to be a bunch of couples and you’re putting your arm around her and acting like a date. You might get through the evening, but it won’t happen twice. Always make sure the woman knows that it’s a date (if it is).

    5. If you don’t know what kind of date to ask her on, you don’t know her well enough to ask her on a date. This is related to point 1b above.

    5a. When planning to ask a woman on a first date (and you do plan, right?), you need to think of an activity that she would like to do, that you won’t fall asleep doing, that allows for talking (since the first date is supposed to be about determining compatibility), and that is non-threatening. This makes Saturday day and Sunday afternoon ideal for first dates.

    Restaurants, movies, and live music venues are lousy for first dates. a) they’re pricey, b) they require the woman to dress up, which she might not be inclined to do for you yet (leading to a “no”), c) they might be too noisy, and most importantly, d) they don’t allow for conversation. Another problem, particularly if you are asking out a woman who dates a lot, is that restaurants and movies particularly are not very inventive as a date venue. Plus, she might want to take her own car if she doesn’t know you well, and most women don’t like walking into restaurants, movies, or live music alone, especially from a dark parking lot. And, movies have the added disadvantage of being threatening: are you going to try to put your arm around her on the first date? If she’s fretting about that, she won’t relax and have a good time (which is the goal of first date, if she likes the time she spends with you, she’ll go on a second date).

    5b. Flying kites in the park, a museum exhibit, a walking tour of the city, a car show, the city aquarium, whatever. Find something that would (or might) interest her, that is not too expensive (or free), and that allows both of you to size the other up, preferably something you have in common. The reason I mention not too expensive is because we all know that you need to go on a lot of first dates to get a second, and expensive will bust you in a hurry. Something a little physical is “interesting,” but too physical will turn off many women, and has the added disadvantage of reducing conversation. In the same vein, don’t go somewhere with a lot of crowds (like an amusement park, fair, etc).

    5c. Pick something that allows casual clothing. First dates break women financially too. If she knows she’s going somewhere that she can wear jeans and practical shoes, she can concentrate on you, rather than her wardrobe and possible malfunctions thereof. “What to wear” is always a problem for women, again your job is to make saying yes easy. If she has to change six times to find the right clothes, it might be too much work.

  16. 38

    Hope this Helps:

    You have made some very valid points- but I have to admit, I’m a woman, and if I were a man reading this very very long and demanding list (assuming I’d made it to the end)- I’d think there’s no point to dating someone if you’d have to walk on eggshells around them. And in your post, you make it seem as though women are the eggshells themselves. I hardly see how that would make things easier between genders.

    And some of the suggestions depend on the woman: for example, you say live music venues are not first date ideas. Well- I saw Patti Smith in the park twice in the past few years- I went with my girlfriends, but if a guy had asked me, I would have gone with him in a minute (not saying that I would have had dumped my girls for a guy, but just saying the live music thing works for me).

    You also say, “The greatest fear that women have is that they will be hurt or killed by a man.” Yes- there are precautions I take to make sure I’m safe. This is NOT my ‘greatest fear.’ I don’t know if this is how you meant to come across- but you make it seem as though all women are living in constant fear of men- and that their main goal is to avoid men.

    Yes, violence against women is a serious problem- always has been. But does that mean I see ‘every’ man as a potential threat? No. But in this post, you make it sound as though women are just a bunch of helpless, scare, PICKY rabbits and the men are the big bad wolves always out to get them. Personally, if I were a man, I’d be put off- especially in this age of increasing balance between the genders.

  17. 39

    It does help. That women worry about getting dressed up is interesting, but to make a spark likely, both people on a date should be dressed to entice. Whether it’s form-fitting for a sporty activity or dressed up for a quality restaurant. Alex’s problem obviously is not that, but maybe something about his style from the start. Presumably not scary or filthy, but maybe too ‘student’ or sloppy, probably with a dose of submissive body language. There could be much more to it, but that would require speculating outside the area of expertise.

  18. 40

    hopethishelps, if I gave a guy my number, I’d prefer he ask me out. It tells me he’s willing to take the time to get to know me and plan accordingly. Otherwise it tells me he’s not willing to go out of his way for me. Or he’s not interested or ready for a relationship.

    Also, if I were at a concert w my friends, for example, I’d want to hang out with my friends.

    Woman like it when a guy goes out of his way for her, it makes her feel special and makes him seem more attractive in her eyes. This doesn’t mean stalking her or bringing her roses on the first date. It can be as simple as calling her up (at a reasonable hour in the evening), saying how you enjoyed meeting her, chatting a bit, and – unless you’re hearing any red flags from her (like if she says her ex husband was just released from prison after serving time for murdering her last boyfriend), ask if she’d like to go out sometime, how’s this weekend.

    A decent woman should be able to appreciate a little chivalry. If she doesn’t respond, then move on, go back to step 1 and find a gal who does.

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