DEAR DR. NERDLOVE: I’m a 32 year old man and my fiancé is a 30 year old woman. She has an 11 year old daughter from a previous relationship. We have been together for 5 years (on and off) but are really happy in every part of our relationship, except for our sex life.

We broke up for about 6 months about a year and a half ago and we both saw other people in that time. We both realized that we really wanted to be with each other and got back together.

I think the time apart changed us for the better and the worse. We both knew that we didn’t want to be in a relationship with anyone else but we came back kind of determined to live our lives how we wanted as we’d seen another side.

I really find her very attractive but after the first few months of being back together and having that honeymoon period again, we went through a rough sexual patch. I was hiding my true sexual needs from her and I was getting frustrated at the vanilla sex. I eventually opened up to her and funnily enough she opened up to me too. We both had similar fantasies so I presumed that we would then go on to act them out together.

The fantasies are; stag and vixen (Hotwife), threesome MMF, foursome MMFM, “cheating” etc etc. You get the idea. I was pleased!!!!

We spoke about it and I got excited. Then it turned out she didn’t want to make it a reality, she didn’t even want to compromise by pretending. She won’t role play, talk dirty, even pretend by text message that she’s into it… just to give me something. She will happily think about it to herself, watch porn about it to herself…. but any involvement with me is being “fake” or setting it up. She wants spontaneity, but not in that way. For instance, if I started talking about while we have sex she’ll get angry and tell me it’s a turn off.

I feel like I’d meet her kinky needs but she won’t try to meet mine, although she actually secretly likes what I’m into.

She wants to have sex to get orgasms. That’s it. Not to have fun. Not to grow closer. She wants me to be “a man” and get on with it. Take her to bed, have sex, explosive orgasms, then go to sleep. There’s no room for play. Experimentation.

Don’t forget we are engaged and I very much love this woman. I just don’t want have to have “boring” sex that doesn’t turn me on, when I feel like we could be having so much more fun.

We’ve gone down to sex a couple of times a month because I just can’t get excited about it. I lose my erection because to be honest it’s just so predictable that I switch off.

I read your article on sexual compatibility and it says you should compromise, but she’s not willing to do it. She said if I want that in my sex life then I should find someone else because she’s not like that. Which means I just put up with it…. but then I’m made to feel like I’m not into sex because I don’t get aroused just because she’s naked. She thinks that’s enough. I should be gagging for it.

What do I do? Is it me? Is it her? Is it both of us?? It’s very confusing because this is my entire life. I don’t want to throw away my relationship because of miscommunication or misunderstanding, or even social pressure to be normal!!

Thank you in advance.

Frustrated Fantasist

DEAR FRUSTRATED FANTASIST: I hate to say this FF, but your fiancé is right. If you want more than vanilla sex, then you’re going to need to be with someone else. Your fiancé has made it pretty clear where she stands: she doesn’t want to have sex the way that you do. And frankly… that’s going to be a problem.

Let’s start with what’s, ultimately, a surface issue.

There’s a pretty big disconnect between how you think of fantasies and how your fiancé thinks of fantasies. For you, your fantasies are literally what you want to do. They’re the side of you that you’ve been holding back from telling her about, lest she freak out at the idea and shame you.

Your fiancé, on the other hand, seems to see fantasies as strictly being the movie that’s running in her head in order to make her orgasm. She may get aroused by the idea of hotwifing or being part of an MMF threesome… but only by the idea, not the actuality. That’s fair; some people have fantasies that may set them off like firecrackers on the 4th of July but they would never want to (or can’t) pursue them in real life. That’s perfectly normal.

But like I said: this is ultimately a surface issue, a symptom of the bigger problem over all. And that’s that, frankly, the two of you are not sexually compatible at all. Your fiancé has a very specific relationship to sex – orgasms and pleasure, period. That’s fine. You, on the other hand, have a different relationship with sex and your sexuality. You clearly enjoy sexual activities that play around with ideas of cuckolding, infidelity and the like. That’s also fine.

However, while these are both perfectly fine relationships to sex, they mean that you two are not suited for one another. The fact of the matter is that you simply aren’t going to have the kind of sex you want with her, and the sex she wants leaves you feeling somewhat dehumanized and used and bored. There really isn’t much of a middle ground to be had, especially considering that she refuses to consider any form of compromise.

The problem is that she’s set up conditions that are impossible to meet. Threesomes, foursomes and moresomes like you and she are imagining don’t happen “spontaneously” outside of porn or people’s imaginations. The gulf between that fantasy and reality means that the odds of this ever actually happening are so remote that you’d have better odds investing your retirement funds on scratch-off tickets.

Unfortunately, you two just don’t work on a sexual level. You may be compatible emotionally and intellectually, but you simply aren’t on the same page, sexually. And that’s one hell of a big but. Missing that sexual component is going to blow up your relationship like Vesuvius on a bad day. Either one of you ends up cheating because their needs aren’t being met, or you break up again because neither of you are happy.

Sex almost always wins in the end, my dude.

Now, you could ask for an open relationship in order to get the kind of sex you require outside of the marriage, if it meant you could keep having straight vanilla sex with your wife. However, not only do I suspect your fiancé wouldn’t be down for that but let’s be honest: you’re going to have to work pretty hard to find someone who a) you’re attracted to, b) who’s down for that kind of sex and c) isn’t going to see the open marriage as a deal breaker. It’s not impossible, but you’re going to be looking for a very rare bird indeed. And to be honest, that sort of sex play tends to require a lot of trust and commitment between partners; that’s a little hard to build with someone who’s just a casual play partner.

If you’re ok with a relationship where sex and sexual compatibility just isn’t a part of your relationship, and your fiancé is willing to sign off on your finding a third… well, that is an option. I wouldn’t recommend it, though. You’re in your early 30s. That’s pretty damn young to be signing on for what is ultimately a companionate marriage.

There isn’t a miscommunication here. There’s no real misunderstanding. You two want very different things from your sex life and she isn’t willing to budge on this.

I wish I had better news for you man, but in the long run, you aren’t going to be happy with her. The best thing you can do is find someone who does want the kind of sex you want. You – and your fiancé – will be happier in the end.

Good luck.

DEAR DR. NERDLOVE: I’m a 23 year old man and I seem to be getting stuck with my dating life. After a few disastrous experiences I’ve turned to Tinder. I’ve met maybe 15 girls so far off this app over 4-5 months. However, none of these girls have ever been interested in meeting again after a first date, especially the 10 or so I’ve genuinely been interested in.

I’m finding it difficult to determine the problem. I don’t seem to be making any obvious or overt date mistakes – the kind that might frequently occur in Tinder date ‘horror stories’. At first I may have been nervous but that’s faded and now I’ve managed to just genuinely be myself and see what happens. It seems that rather being the subject of a ‘horror story date’ I may simply just be ‘unmemorable’.

I often simply hear “You’re a good looking guy but not my type” and “You are a really nice guy but I don’t feel any chemistry”. I know that these may just be generic rejections but it’s even come from girls I’ve thought must surely be interested based on positive body language etc. My own-self reflection on my experiences has me musing that I may be boring and not charming, not flirting enough or good at flirting, not escalating or unconsciously giving off the wrong vibes such as seeming unconfident or desperate. For example, I’ve never attempted a “first date kiss” at the end but conventional advice seems to suggest that it SHOULD be okay to wait to kiss until the 2nd or even 3rd date.

What could I be doing wrong, Dr. NerdLove? It’s hard seeing how easily people around me seem to get into relationships or have genuine interest from girls while a consistent streak of no second dates must surely signify an issue.

Stuck On First

DEAR STUCK ON FIRST: You said it yourself, SOF: you’re not flirting and you’re not making any attempts at building any chemistry or interest. It’s one thing to want to take things slowly and make sure that you’re not about to subject your date to some OKCupid nightmare, but there’s also such a thing as being SO safe that you give the wrong impression. The fact is, you’re giving off signs that you just aren’t interested in them; I imagine that they may be a little surprised that you asked for a second date at all.

Now this doesn’t mean that you need to start being Handsy McGrabsALot or trying to perform an amateur tonsillectomy with your tongue as soon as you meet your date, but you do need to give some indications that you actually want to date these women. Some of this is going to be in flirting and showing that you like them as a potential lover. You want to build that chemistry and sexual tension after all. And some of it will be showing that you want to kiss them, even if she would rather wait for a 2nd date.

But I’m gonna be honest with you dude: while there are women who don’t kiss on the first date, the majority do – at least, if the date was enjoyable. When in doubt, you can always at least make the offer and let her decide how to play things.

Now having said all that, I want you to keep in mind: despite how it may feel right now, you’re doing really well. You’ve gotten a metric ton of dates lately. That says a lot about you and your desirability. You’re at a plateau now, that’s all. You just need to work a little harder – make some mistakes and learn from them – and you’ll get break through to the next level of your dating life.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com)

DEAR DR. NERDLOVE: I am a 26-year-old male who has never had a girlfriend and is a virgin. I realize this might seem weird, but various circumstances (being shy in my teenage years, not feeling ready, being busy with university, etc.) put me into this situation. Also, deep down I might subconsciously have thought “nobody would like someone as me, so why even bother?”

Reading your book and listening to your podcast made me realize that indeed there is a chance for everyone if they are just willing to take it. When 2016 turned to 2017, I made a promise to myself that I would actively make an effort to meet new girls and seek out a girlfriend. I started with Tinder and a few other dating apps and quickly realized that it wouldn’t be easy. I did not expect tons of matches, but nonetheless I had hoped for a bit more.

Using dating apps has been quite stressful, because I get so few matches (maybe a few every second week or so), but THEN it’s not guaranteed that the girls will actually answer me — ghosting has been a big issue for me.

I have tried with various opening lines such as “If you were a superhero, what super powers would you have?”, “If you had a time machine, where would you go?” I even tried out your “Soo … ninjas or pirates”, but only got a few vague responses. It seems so arbitrary. And the waiting part is the worst.

Anyway, since January I have actually managed to get on a date with four girls (just casually walking/talking in a park for a few hours). Since I have never dated anybody before, this is 400% more than I’ve ever done in my entire life, but still, I would have liked to be one more than four dates during these ~8 months since I started. With the first three girls there were no chemistry whatsoever (but hey, I learned a few things about how to date!), but then there were this fourth girl who turned out to be really nice and had a lot of common interests with me. When I walked home, I had a really good feeling. Sadly, when I later texted her saying “thank you for a good date; would you like to meet again?”, she told me that I was a nice guy but she didn’t really feel it. I was devastated, since to me it feel so close to actually have a chance for a real relationship. But knowing about the Oneitis has helped me to move on.

So … I am not sure what actual advice I am seeking other than “hang in there!”. I know that there are other ways to meet women, but I have found that going to clubs and bars is not for me, since I feel a bit awkward at such places, especially if there is loud music. I find it really difficult to casually walk up to a girl and initialize a conversation. It’s way easier for me online.

I have done many things to improve my dating profiles, both with my pictures and my bio text. I have asked for feedback both from friends and strangers online. I also used sites like Photofeeler to get a better idea of my profile pictures (I am maybe slightly-below average-looking). I also went to a forum for women and asked what they thought about my pictures. I was told that I looked like a nice, cute guy — but I looked more like a friend that they would want to hug instead of having a romantic relationship with. As if they can see my inexperience with dating in the way I look.

I never thought that finding a girlfriend would be easy, but I am feeling a bit depressed about the whole situation. I don’t think I am picky or anything; I just want a nice girlfriend who is friendly and wants to share her life with me, maybe travel around a bit, etc. I have tried so many dating apps and websites and the outcome is so minimal that it’s making me sad. The other day I actually thought about making a “Hello, would you date me?” image and share it on Facebook, hoping that somehow I would meet a girl through a common friend or something. I am in a stage where I cannot judge if this seems to desperate and would actually harm me instead.

What should I do?

Kind regards,

I Just Want To Date

DEAR I JUST WANT TO DATE: First things first my dude: congratulations! You have made huge leaps to get where you are today and that’s something you should really be proud of. You have, hands down, made progress and gotten to a point that you’d never thought you could before.

So here’s what’s going on: you’re hitting the pain period. This is the point everyone goes through when they’re starting out. You are suddenly, insanely aware of just how awkward you are at this. Like a newborn giraffe, you’re stumbling along on those spindly legs and falling down over and over again. This can be incredibly frustrating; even though intellectually you knew this was all going to take time, there was that part of you that was hoping to hit the ground running. There’s always that dream that, if you just started trying, you’d realize you would discover you had a previously undiscovered talent or superpower and now you’d be a dating phenom.

Unfortunately, while that makes for popular manga tropes and cheesy sports movies… real life doesn’t work that way. You are, for all intents and purposes, building up your social muscles. This means that not only are you NOT going to be lifting the heavier weights right off the bat, but there’s gonna be pain. You’re using muscles you’ve never used before. You’re stretching them out, pushing them past your old limitations. Just as a hard workout means you’re going to be sore the next day, you’re going to be dealing with that mix of unfamiliarity, awkwardness and anxiety that you’re feeling.

But the good news is: this starts to pass. As you get more experience, you start to get more comfortable with the process. As you start to meet more women, you quit focusing so much on The One because you realize that there is no One; as great as that person was, there’re other women out there who’re just as good and who are into what you have to offer. And just as importantly: you start to recognize your own progress and learn from it.

I mean, dude. You’re getting regular matches. Not as many as you might like, true… but you’re getting them pretty consistently. That’s good. That’s a solid start. Same with having gotten some dates. That is also good. That’s progress.

Now here’s what I want you to do. First: pare down the number of apps you’re using. Spreading your attention too far and wide is only going to make you more stressed. You only have so much mental bandwidth, and trying to pay attention to too many things at once just drains it faster. Stick to one or two at most.

Second: now that you’ve got some results, it’s time to A/B test. That is, I want you to change up your profile and see how people respond. Do you get more matches when this photo is your primary online dating photo or this one? Take some new ones – maybe with a professional photographer- and consider the story that your photos tell about you. Highlight and prioritize some areas, and deprioritize others.

You also need to consider what vibe you’re sending. Right now, you’re hearing from a lot of people saying you look like you’re cute, but more “friendly”. Some of that makes me think that you’re still being shy and hesitant and possibly giving off a neediness vibe… especially when you talk about sharing a photo on Facebook like you’re looking for a lost puppy. This is an attitude that’s going to turn women off. People have enough to deal with in their life without taking on the responsibility of managing the self-esteem of someone they don’t know yet.

You need to be willing to be more assertive and confident in your presentation. If you’re hitting the “I want a girlfriend” thing hard, try dialing it back and focusing more on sending a vibe of “I have an awesome life and I want to meet equally awesome people“. You have to believe in your own value when you want people to date you because, frankly, if you don’t, then why should they?

The other thing: stop checking your app constantly. They all have notifications; you’ll know when someone matches with you and when they respond to you. If you’re going to do the online dating thing, you need to take a “fire and forget” approach or you’re going to go insane. Not everyone is going to be online at the same time, nor are they necessarily going to respond to your message immediately. People get busy with life. They get overwhelmed with the messages they’re getting. Hell, sometimes, just getting a message makes them anxious and now they’re trying to work up the guts to respond to you. Sitting with sandwiches by your phone while you’re staring at Tinder like Gatsby staring at the buoy in the bay is going to drive you insane. Swipe a few, message a few, then close the app and go about your day. The messages will be waiting for you when you check back later after doing whatever awesome thing you’re going to be doing that day.

Don’t forget: you’re still starting out, man. You’ve made huge leaps. Don’t get down on yourself because you aren’t ready for the Olympics after your first month of training, ever.

You’ll be fine.

Good luck.

DEAR DR. NERDLOVE: I met this guy two months ago through common friends. He has been texting me ever since everyday. We have great connection and chemistry, but he never asked me out on a date.

He goes to med school and has to work at the hospital 8 hours per day so he’s kind of on a tight schedule but still he manages to make time for his friends and never asks me to come along. Sometimes he meets me wherever I am but never makes the effort to ask me out alone with him. Once I decided to stop talking to him and he sent me a huge text to understand what’s going on and to explain to me that he doesn’t want us to stop talking.

I don’t understand the mixed signals and the lack of effort and I really want him to step up his game because I’m starting to have feelings for him. What should I do in this case? And how can you explain this behavior? 

Waiting In The Wings

DEAR WAITING IN THE WINGS: There’re two things that explain his behavior.

First: dude’s in med school. That is going to take up pretty much 99.999% of his time, energy and mental bandwidth. He is being run ragged right now and that’s only going to increase as he graduates and starts interning and becoming a resident. So this means that his time is going to be on a serious premium and he’s going to be extremely careful about how he spends it.

Second: well, I hate to say this, but I don’t think he’s that into you. Don’t get me wrong: he likes you. He likes talking to you. He clearly thinks you’re cool. But there’s nothing about what his behavior that sounds like he’s actually into you on a romantic or sexual level. Men`, for the most part, are going to let you know if they’re interested in dating you. You’re going to run into the shy ones on occasion – especially when you’re dealing with nerds – but a lot of them tend to be proactive. If he’s not trying to make time for the two of you to get together, and is passively coming to see you when you ask?

That’s generally a sign that he’s not feeling the same things you are.

Now if you want to see if it’s a case of cute-but-clueless or sweet-but-shy, then you can call the question. Ask him out on a date – not “hang out”, not “maybe do something”, but a straight-up, explicit, no-way-to-misconstrue-this date. Maybe this’ll be his “come-to-Jesus” moment where he realizes that you’ve been sending signals he’s been missing. Or maybe he’ll have to give you the explicit “let’s just be friends” talk that he’s been trying to just imply up to this point.

Either way, you’ll have your answer. And then you’ll know what you need to do next.

Good luck.

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com)

DEAR DR. NERDLOVE: I found your website after searching for an answer to my problem for hours upon hours on the internet. After seeing some of the advice you gave out, I decided to give it a shot and see what you had to say about my particular problem. You had touched on it a bit in some of the other articles, but there were always key differences that just seemed to change the circumstances in my opinion. So here it goes.

I met this girl a while back through a family member she went to school with. At first we just kind of knew each other and that was about the end of it until we started to text then later hang out, always as just friends. Eventually, we got closer and closer until we were spilling every secret that we had. We both know things that nobody else in the world knows about the other. We get along great, have similar personalities, senses of humor, and interests. We became best friends without a doubt. But then she dropped a bomb on me when she said “If we were both older, you would be the guy I would want to date.”

Now before this, I had thought a bit about the whole dating thing but just dismissed it as a passing fancy. But she kept dropping little lines like this until it became more than that. Eventually, I told her that I actually had thought about it and would honestly like to date her and see where it led. But if you thought that is as thick as this plot gets, you’re sadly mistaken. During this whole time together, she has had a boyfriend.

The guy is no good for her and she complains about him constantly, but still refuses to break it off with him. This is even his third chance with her. I believe I’ve made my feelings clear about her and yet she tells me that she is afraid to be alone and that’s why she won’t just dump him. But he honestly just doesn’t even care about her. She is super easy to make happy, but he won’t even take the time to text her everyday. The only reason I know this is because we are talking on FaceTime literally every night. He won’t make sacrifices for her that I have on a regular basis, but he is still the one she stays with. But the worst part is that through all of this, she still says things about dating me, but says that I shouldn’t be as nice as I am because I’m not her boyfriend. She loves that I am chivalrous when we hang out, but gets upset when I pay for lunch or open the truck door for her. Through all of this, I’ve held back from straight out asking her to go on a date out of respect of their relationship, but at this point, I’ve become more of a boyfriend than he has ever been to her. But I’m starting to lose my mind here. I’ve already changed so much for her (quit smoking, started eating better and exercising, made new career choices, etc.) but she just refuses to give me a shot, choosing instead to stay with someone who won’t even text her good morning most of the time.

The thing is, I just have no clue what to do. I really do love her, but at the same time, I don’t want to lose her as a friend. I just don’t know if I could be JUST her friend. I know it sounds like I’m justifying my staying in this relationship by making it sound like there is a chance that we could be more than friends, but she talks about what it would be like if we were dating or if she were my girlfriend all the time. So I have a hard time believing it is all in my head. I just don’t know what I should do, or even what I can do. I would appreciate any advice you have to offer. Hopefully I’m not just completely screwed or anything.

Thanks in advance, 

Confused As Hell

DEAR CONFUSED AS HELL: I get a variation on this question basically every other week now, and they all more or less follow the same script. And when I try to be nice about what people should do or couch it in softer terms, I get a lot of arguments about why they should or shouldn’t do such and such. So, my dude I am going to give you the only advice you need right now.

Fair warning though: you’re going to hate it. You will get five lines in past the intro and rage-quit reading. You’re going to wonder why the hell you wrote in to me when you see this. But this is going to be the best advice you will ever get. It’s Chair Leg of Truth Time.

My dude, you need to make a move or get off the field already.

You need to decide if you’re going to take your shot by actually asking her out on a date or give up and move on. You’re hanging around in this limbo state, a point of quantum uncertainty where you both do and don’t have a chance. But you’re staying in this place because to make a move would collapse the quantum waveform one way or the other and, let’s just be honest: you’ve got a pretty good clue what the answer is gonna be.

Now here’s are a few things in particular I’m going to take issue with.

First:  “I’ve become more of a boyfriend than he has ever been to her”

No, man. You’ve been her friend. Maybe a close friend. Maybe an intimate, one of her confidants. That doesn’t make you a boyfriend. Don’t round this mess up just to have something to tally onto your list of grievances against her.

Next: “I’ve already changed so much for her (quit smoking, started eating better and exercising, made new career choices, etc.)” 

No. NO, no, no, no. You are not going to pass any of this off on her. Those changes you made? They’re for you. You do these things for you, because they make your life better, not because they’re your entry point into her pants. She didn’t ask you to do them. She didn’t make them a requirement for your being friends with her. She didn’t say “quit smoking, get a new career and maybe I’ll give you a chance.” You did those on your own, for you. Self-improvement isn’t something you get to pass off as “well I did these things, now you owe me a chance.”

And then: “She refuses to give me a shot.” 

No. Sorry, I’m not going to let that pass. “She refuses to give me a shot” implies that there is in some way, shape or form an obligation for her to give you an opportunity. And no. That doesn’t exist. That’s Nice Guy territory and you never want to go there, Simba.

Here’s the thing, man: she may well be miserable dating this guy. You might indeed be the kind of guy she’d want to date. But while you may be the KIND of guy want to date, you’re not THE guy she wants to date. Because, quite frankly, she isn’t dating you. It’s not as though you’ve been subtle. You’ve had these conversations. She has yet to break up with him for you, which should be all the indication that you need.

And just to head you off at the pass here: this isn’t about “women love a

holes”. If we take her at her word that she’s not happy with him and everything is awful, then the fact of the matter is that she’s not ready to leave him. And that can take a while. Leaving a relationship, even a bad one, can be freaking difficult. She’s not going to leave until she has reached the point where staying with him is worse than the alternative and that might take years. If it happens at all.

Another thing to consider: if she were to break up with him tomorrow, she’s not likely going to turn right around and date you. She’s given him three chances now. If things are that bad and she has passed on breaking up with him three times? Then she’s going to have her own stuff to work out before she’s really going to be in a place to date anyone. Even if you were a viable option, she’s going to need to be taking time away from relationships and dating in general.

Another possibility? She’s not as upset as all that.

She may be blowing off steam. She may be appreciating that she’s got you dancing in attendance on her, being the sympathetic ear to her drama.

Or what she’s saying and what you’re hearing are two different things. She may be complimenting you, but “you’re a great guy” and “you’d make someone a great boyfriend” aren’t the same thing as “you’d make a great boyfriend for me.” And if she is saying “you’d make a great boyfriend for me,” you may well be missing the silent “…if I were attracted to you.”

So.

If you’re still reading, you’re probably wondering why, having told you all of this, I told you to ask her out, lo those many paragraphs ago.

That’s because you need to cauterize this wound. Until you get your answer, until you collapse this wave, until you take a damn stand, you will spend all of your time and energy on this and never go anywhere. This relationship will eventually come to an end and in the aftermath you will realize just how much time you wasted doing nothing. By asking her out, you cut the bulls

t. You will save yourself years of moping and heartache and pain and time that you could have spent dating people who want to date you.

So it’s time to quit this passive-aggressive “well, I have feelings for you but I won’t actually ask you out” nonsense. It’s a stalling tactic. It’s not out of respect for their relationship. Trying to couch this in terms of respect is bull and you need to have more respect for yourself than to try this. You told her you have feelings and want to date her. The only difference between that and “Will you go out with me” is that one is passive. You laid it out there in hopes that she’d pick it up for you.

Well. She didn’t.

So now you have two choices.

The first is that you straight up ask her out on a date. No “well I would totally date you if.” No “I have feelings for you.” Just a straight “I want you to break up with your boyfriend and date me instead.”

The second is that you admit that she may like you, but she doesn’t like you the way you wish she did and you let this go. And that means no sticking around, trying to be her friend when you know you can’t. No waiting for her to break up with him in hopes that the window will be open long enough for you to climb in.

You end this. You forgive yourself for loving if not wisely then well and you move the hell on. 

And if she says no? Same story. You take that no for what it is: no, she doesn’t want to date you. Not “not right now”, not “no, but maybe in the future.”

It will suck. You will hate it. But you will have gotten your answer. There will be no more ambiguity. No more nights of wondering “what if”. Now you know. And in knowing, you won’t have to waste any more time on a dream that can never happen.

I know. You hate me right now. You’re angry.

But believe me: I have been where you are, I have done what you’ve done and I’ve got the emotional scars to prove it. This is what I wish someone had told me back in the day. And so, as cold as it may sound, as harsh as it is, I am giving you this advice.

Quit stalling. Ask her out and take the L that is likely in your future. Or move on.

Either way: you’ll be much happier in the long run.

Good luck.

DEAR DR. NERDLOVE: I’m a 29 year old male and primarily date online these days. In my earlier twenties I read a little pick up artistry from one David De’Angelo, who liked the “Cocky and Funny” school of thought. So I would go out to local malls and such and try these sorts of techniques. I had some nice conversations but most I approached were attached. Go figure.

Anyway, I told a buddy of mine about my little experiments and he pointed out that I could approach someone who had a boyfriend, who might not take very kindly to some nerd hitting on his girl. Basically, I could get my butt kicked by a Neanderthal. Apparently this sage bit of advice sunk in because I quit approaching people offline (well, that and people online were more likely to be actually single.)

So, is this a rational fear? You’ve approached way more people than I have, so if it’s gonna happen it would have probably happened to you once or twice. Have you ever had a guy get in your face over accidentally approaching “his” girl? (I don’t like that term but for lack of a better word.)

I ask because the online method doesn’t seem to be working for me these days. It’s pretty slim pickings here. I’m in a rural area, for context. So maybe it’s time to try approaches offline, but I have major approach anxiety, in part due to this fear I have.

So what do you think?

Thanks,

Anxious in Ohio

DEAR ANXIOUS IN OHIO: In all the thousands of approaches I’ve made, in all the times I’ve approached women who had boyfriends, girlfriends, husbands and very protective fathers and brothers, I have never gotten my butt kicked. Nor have I had Big Moose try to pound me flat because I tried to talk to Midge. I’ve had guys in clubs try to out “alpha male” me in weird passive-aggressive ways, but it’s never come even to threats of violence.

(I did, in fairness, once get threatened with a Lochaber axe, but that was an entirely different situation.)

In fact, I’ve had more near-misses with violence from drunks trying to pick fights, which had nothing to do with any of the women I talked to.

Also one clown with a gun. But again: entirely different situation.

Point is: most people aren’t violent. You’d be more likely to get the “you talking to my gurl” schtick in high-school than you are as a grown-ass adult and especially in places like malls. Unless you are seeking out women in astonishingly aggressive areas – trying to pick up chicks at a Hells’ Angels bar, for example – I don’t think you really have much to worry about.

99 times out of 100, if you try flirting with someone who has a boyfriend, a simple “Oh, ok, cool, sorry to bother you,” to her (seriously, women hate it when you apologize to their boyfriends for hitting on them. It suggests you see it as an insult to him) will settle things perfectly well.

And that 1 time out of 100, you can probably talk your way out of it anyway.

Good luck!

Please send your questions to Dr. NerdLove at his website (www.doctornerdlove.com/contact); or to his email, doc@doctornerdlove.com)