DEAR DR. NERDLOVE: 

I am having a bit of a problem with online dating. I don’t know exactly how to make a conversation exciting enough which would lead to a date. All I do is simply ask basic get to know you questions such as where are you from, what do you do for a living etc. The end result is always the same… either they lose interest or else I get bored and give up on the conversation entirely. Other times I ask them out and they say that its too early.

The only question is how do I simply make an online dating conversation worth my time and my match’s time? I am trying to invest my time in online dating because chatting up women in clubs and bars is something that I find terrifying. To tell you something about myself I am an introverted 27 year old guy who has never had sex and who has only kissed 1 girl in his life. I find it hard to come up with a conversation sometimes or banter/jokes to keep a conversation stimulating. I have friends and work mates who are awesome and I have hobbies and interests and have travelled sometimes so I am not exactly someone who has never set foot out the door.

Can you please assist?

Thanks again

Frustrated Somebody

DEAR FRUSTRATED SOMEBODY: Your problem is right there in the letter, FS; you’re asking really basic questions and everyone’s getting bored. That’s the entire issue. When you’re trying to meet people via online dating, you don’t have a lot of the same options that you have when you meet people in person. There’s no chance to build intimacy via touch, no way to build a connection through physical excitement. All you have are your words to woo women and as a wise man once said: the purpose of language was to woo women and in that endeavor, laziness will never do.

The point of online dating is to meet people in person. To do that, you want to give them a reason to want to see you, to be excited to meet up with you. And if you’re just asking boring questions… well, they’re gonna get bored and decide they want to  see someone who’s more interesting.

Now that doesn’t mean that you can’t ask “getting to know you” questions, nor does it mean that you have to be putting on a performance to get her to like you. But you do want to flirt and be entertaining so that she enjoys talking with you and wants more. And when it comes to language, the easiest way to be more attractive is to be fun to talk to. One of the surest ways to be more fun and engaging is through humor.

Of course, there’re all kinds of ways to do this. You can be playful in your flirting; since apps like Tinder now let you send animated gifs, you can use those to create playful banter. A Spongebob meme or Archer saying “Hey, phrasing” can be a way of playfully engaging with what she’s said by having an exaggerated overreaction.

Alternately you can play games “two truths and a lie”. Or you can find ways to react to things that she put in her profile. A Harry Potter reference could lead to, say, joking about the two of you having to write and direct a new Potter film and the conflicts that would result (because of the simmering sexual tension).

You say that you have a hard time coming up with banter or jokes to keep the conversation stimulating. There’re a few ways to learn how to be better at bantering or good at having the right thing to say at the right time. The first is to learn to stop trying and just start going with the flow. Improv classes might be worth your time here; you want to learn how to be in the moment and how to react instead of trying to plan for every contingency or find the most clever thing to say. The best flirting humor is often the least planned; when it feels forced, it’s rarely as fun or organic.

But the other is to immerse yourself in humor and things that you think are funny. That may mean mainlining comedies and stand up specials on Netflix as you try to get a feel for the rhythms and pacing of jokes and story telling. It may mean a steady diet of funny authors like Terry Pratchett or Carl Hiassen. It may mean paying attention to naturally funny people like Ryan Reynolds or Ali Wong, Mel Brooks, Craig Ferguson or Kevin Hart. The more you pay attention and learn from them, the more you’ll figure out the styles of comedy and humor that work best for you and for your flirting style.

These will make you more fun to talk to and that, in turn, will make it easier for you to keep up the emotional momentum you need for successful flirting and dating.

Good luck.

DEAR DR. NERDLOVE: I really appreciate your ideas on dating and social interaction in general. Too bad your channel wasn’t up 20 years ago, that would have prevented a lot of heartaches.

Which leads me to my current situation. I’m in my late 30s and developed a crush on a new co-worker recently. It came very unexpected and the last time I felt this way was over ten years ago. At first I was somewhat amused about my feelings and expected them to go away sooner or later. I enjoyed spending time with her at work and we became Facebook friends.

That was one month ago. We haven’t seen each other lately, but I’ve developed a form of Oneitis since. I became obsessed with what she posted, who her other friends are and how she reacts to my posts. Because I’ve struggled with similar situations in the past, I was looking for ways to get her out of my head. And that lead to the stupidest idea ever: I unfriended her on Facebook. I regretted my decision immediately but as you probably know there is no way to undo this one button click.

Best case would be that she doesn’t really notice, worst case that I hurt her feelings and made the situation thousand times worse.

Now I’m thinking of ways to get back to normal. I could send a new request and tell her that I unfriended her by accident. But would she believe me? Or I could wait and see what she tells me the next time we meet each other, probably in two weeks, when a mutual friend of ours will have a gig with his band. And after that we will still have to work together from time to time. What bothers me is that I sometimes have the tendency to push away people that get under my skin. I really think I can get over her and just have a work relationship or friendship with her. But I just don’t want to make another bad decision.

Thanks in advance for your time and for your feedback,

Friends or Not

DEAR FRIENDS OR NOT: Yeah, you kinda overreacted here FoN. You had a lot of other options to limit just how much you saw of your crush. You could’ve set up groups and filters on your Facebook page that would let you see folks you wanted to see but not show you as many posts of hers. You could have set her posts to a lower priority so that they didn’t show up in your feed as often as other, closer friends. You could have snoozed her for 30 days, which may have been enough time for you to process those inconvenient feelings and get to a place where you weren’t feeling so obsessive about her. You could also have just muted or unfollowed her, which would have kept her posts out of your feed but kept your connection on Facebook, allowing you to quietly refollow her at a time of your choosing.

But it is what it is and you did what you did and there’s not really a graceful way of undoing it.

However, while there isn’t a graceful or subtle way of re-friending her… it’s not irreversible, or even all that bad. Mostly you just have to be willing to eat some crow and deal with her knowing that you unfriended her and now you want to refriend her. But there are still ways of managing that that don’t require you to say “yeah, so I kinda got obsessed with you…”

One of the (few, dubious) benefits of Facebook being such a black box system is that it glitches and f

ks up in any number of ways. If you were to, say, re-friend her and just tell her “yeah, I noticed that some of my friends got dropped from my account,” the odds are pretty good that she wouldn’t question it at all. Alternately if you tell her that you were paring down your friends list and she accidentally got caught up in the mix, she would probably take that at face value.

But honestly, the best option would be to leave out the excuses and just say “Yeah I unfriended you and didn’t mean to,” and leave it there. Unless she is absolutely, totally monkey-s

tting bananas about social media and monitors her engagement and friends list like a hawk, I doubt she’ll give it more than a second’s thought before reaccepting you as her friend online.

And then if you find you’re not over her yet, you can immediately snooze her profile for 30 days and give yourself some time.

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: About 4 years ago i met this amazing woman in the gym we were both attending in Paris. She was extremely kind, empathic, caring and everything one hopes to find in a S.O. We started chatting and within a month we were dating. I was still a virgin when i met her (aged 21). It wasn’t that I was that shy nor that I didn’t have dates, for some odd reason I hadn’t lost my virginity until then and I wanted to lose it with someone that I trusted. She was that person.

Everything was good but there was a problem: Me. I am an insecure asshole. Soon after we started dating I became very jealous of her, particularly her past (after all, she got to have sex before me while I had to wait 21 years, which just kind of make me feel inadequate) and her present. I just didn’t like that she was my first while I wasn’t hers. I also had a morbid curiosity in being with other girls too and “recover the lost time”.

We were both taking the relationship very seriously, and I felt like I was going to marry her someday (she was a bit older than me and we had actually talked about it a few times), something I had mixed feelings about because she was amazing but at the same time I wanted to have a past of my own and experience other women. I just regretted really she being my first and having found such a great person at first try.

As a result we always had a problematic relationship. Every now and then I would turn ape s

t crazy and freak out over details of her past sexual life or be jealous of her male friends. All because I wanted to have had experienced it too. For the most part we actually had a great relationship, we communicated really well and we were very close. But of course, me ruining the relationship with these pathetic scenes would deteriorate the relationship, no matter how good the rest was.

Now, this girl is a f

king saint. We were in this for 4 years! She always waited for me to “heal” and change. It eventually grew better but it never completely went away. A few weeks ago everything changed: She was talking to a male friend of hers who came out of town and who she views as almost her “brother” in the bedroom next to where I was for a few hours. No problem for me there. But then I heard something “suspicious” and I became convinced they were having sex (even though everything was 100% normal when I confronted them). That was enough for her. She broke up with me. Finally.

She told me that we were over for good. That there was 0 chance of us getting back together, even though she still had feelings for me. She seemed very convinced of this. I was hurt but I agreed. I’m an idiot and I never meant to hurt her, but she gave me enough opportunities to change and I didn’t take them. All my fault. So I moved on, I still loved her and wanted her back, but I knew there was little chance we would get back together.

For the first few days i was in grief. I wasn’t in the mood to go chase someone else. I wanted to meditate about myself and I felt it would be disrespectful and inappropriate to just go date someone else right away. I chatted with girls and even had one very interested in me in a party I went to, but i didn’t take the opportunity to mess around.

My ex didn’t feel the same way. She claims she thought that our relationship was 100% over. So less than 2 weeks later she was already having sex with a guy she had met even before we broke up.

About 3 days or so after she had sex with this dude I contacted her I didn’t know about it then) because I wanted to talk and I had to pick up some stuff I had in her apartment (and also, hopefully, manage to somehow convince her to come back to me). While we were apart, I actually came to realize how awesome this girl is and how much I actually love and how stupid my insecurities are, and how I actually would like to marry her someday. She tells me she had sex with this guy because she was trying to move on, as she thought it was really over between us, but she realized that she was actually way more in love with me that she ever thought and that she wants me back.

Frankly, I deserve it. I didn’t treat her 100% right, she took a lot of s

t because of me. I risked it and here’s my payment.

I was very hurt to find out about it, even though I thought it would have been a possibility. For once, I don’t get why she would be so quick to date someone else after only 2 weeks break up. She says she loves me but I don’t think she would be so quick to rebound if that was the case. It’s as if our 4 years together meant nothing to her. It makes me doubt of her character and makes me think she was already cheating on me with him or thinking about it (she says it’s not the case, that she never wanted to be with him while we were together). She says she’s going to talk with this guy and tell him she’s not interested anymore.

Secondly, even though she says she’s done with this dude, she doesn’t look so sure about it. She seems confused. When I went to her apartment she actually had a coffee date scheduled with this dude for that afternoon. She called it off, but she told me I had to “decide myself about getting back together” as if she was counting on me to tell her yes or no so that she could just go back to this other dude or ditch him. She says it wasn’t the case. I’m not sure.

Lastly, I’m no good for this girl. Let’s be honest. With my jealous history it would be very hard to me to get over this rebound fling of hers. I would probably blame her for the last of the relationship. I would really have to be the “better man”, something I’m not sure I could do. I don’t want to hurt her anymore. Besides, as far as I’m concerned she may not really love me. She’s been 4 years with me. 4 years of attachment is something hard to get by and it’s only natural she thinks she “misses me” after she’s been with someone else and didn’t feel the exact emotion of validation she was used to feel. But in reality, deep down, it’s all an illusion based on habit.

I really don’t know what to do, Doc. I love this girl and I miss her. Part of me wants back together. But this relationship is probably just so shattered already, is not worth saving. Some things are just better off dead. This dude she had sex with seems like a good guy who likes her. I just want her to be happy, maybe he’s the best option. As for me, I probably need to meet other girls, live a little bit. Maybe in a few years, if she’s free and I’m free and we’re both on the same page we could *potentially* work. Or not. I wish things would have been different. But I know I’m the one who’s mostly to blame for this.

What do you think I should do? Should we try again? Spend some time together as friends and see how it goes? Or just go against my first instinct, break the girl’s heart and tell her it’s over for real?

Second Time Lucky

DEAR SECOND TIME LUCKY: Alright STL, I’m going to level with you:

No. You should not get back together with your ex. In fact, the best thing you can do right now is to take a step away from dating in general and her in particular.

When people ask whether or not they should get back with an ex, I have a couple important questions.

First: When did you break up?

Second: Why?

Third: Did the circumstances that caused the break up actually change?

There are a few factors involved here. The first is how recent the break up is. When you’re still in the early stages of a break-up, especially it was a long-term relationship, then that desire to get back together often has more to do with the fact that your status-quo has been shaken up more than feeling like you are better together than apart. Humans on the whole prefer stasis to change, and a break up – even a necessary one – is a big change. The longer you’ve been together, the bigger the change; you’re functionally having to learn how to be single again and unlearn the habits you developed in your life together.

Your memories can also screw with you; it’s very easy to discount the negative memories and focus mostly on the positive ones and get caught up in that glow of nostalgia.

So we come to the second question: why? Why, exactly did you break up? Was it a case of circumstance? Were you in the wrong place in life to have a relationship with this person? Did you have needs that weren’t being met? Conflicts that couldn’t be resolved? Or did someone blow the whole thing apart with their actions?

A little self-reflection is incredibly important when it comes to deciding whether to get back together with your ex. After all, if you don’t have the distance and the perspective to understand just what happened, you aren’t going to do well when it comes to that third step.

After all: if things haven’t changed – if the reasons you broke up are still in effect – then getting back together is just going to be the ten minute dance remix of why you broke up. Except this time, the chances of being friends afterwards will be even more remote.

With all that in mind, we come to your situation. Your breakup was fairly recent and it was because, frankly, you were an insecure bag of slop who kept accusing his girlfriend of infidelity because you couldn’t handle the fact that she had a past before you two got together.

But here’s the thing: you haven’t changed. Your past issues with her aren’t in the past. They’re still very much in the present. You are still treating her the way you did while you were together. I mean, s

t, you just got done telling me that you’re half-convinced she was cheating on you with this dude and you doubt her character for her fling.

And look, I get it. It stings to find out that your ex has been with someone else. It hits that part of your brain that asks “what does this say about me?” But the answer is almost always: “nothing”. What it says about her though, is that she just broke up with a dude who was always accusing her of cheating (or planning to cheat) and one of the ways to get over that frustration is to just say “ok f

k it, I’m going to go just have a fling with someone I know and trust”.

In short, it had far more to do with wanting to put s

t in the rearview mirror for her and far less about her having kept this guy in the wings.

But like I said: the things that broke you up are still very much in effect. Quite frankly, a few weeks of having a sad about having broken up are not going to be enough to get over some deeply seated insecurities. I am here from the future to tell you: you will be together for a week or two before you have a fight over her fling. And let’s be real: nobody wants to relitigate the Ross and Rachel “We Were On A Break” case.

However, dating around isn’t going to solve anything for you either. Your problem isn’t your inexperience or the relative lack of experience you had in relation to hers. The problem is how you handled things. While a little envy is understandable – hey, who wouldn’t like to have had those amazing experiences with their partner? – you took your insecurities and made them her problem for four years.

That sort of thing is relationship poison. And quite frankly, this is going to hit every relationship you have until actually address it. Not by going and having all the crazy adventures you wish you’d had, but by talking to a counselor or therapist. These deep-seated insecurities are going to eat away at any relationship you have. Having more partners isn’t going to fix things; at best, you’re going to be treating the symptoms, not the cause. At worst… you’re just going to feel like it’s never enough. There will always be some new thing that you will see as “well, if I could just have this, I’ll be satisfied.” And no. No you won’t. You’ll be tossing experience after experience, person after person into a deep, dark hole that will never be filled.

If you don’t want to have a repeat of this relationship – whether with your ex, or anyone else you may date – then you really need to start the recovery process and root out the cause.

So while I get that you miss your ex, and she misses you, you aren’t really in a position to be dating anyone right now. The best thing you can do for yourself is take time to really work on yourself. And I mean really work on yourself, with someone who can help you handle these issues.

If, after time has passed, you’re doing better and you find yourself in touch with your ex again? Well, maybe you can see where things stand. It may not be another chance at romance… but maybe you can be friends again. And maybe seeing her again will be the motivation you’ll need to do the work.

But until then? Getting back together with her would be a bad idea. Don’t subject yourselves to a repeat of the misery you both have gone through. Focus on yourself for a while, and get yourself back into emotional health.

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 love reading your articles, and have a question for you that may be less applicable for your usual audience. But you’ve written before about virginity and toxic gender stereotypes, and I think your advice is always spot on.

Here’s my problem: I’m a nerd who’s never really struggled with dating until now and faith has been formative in my life. I grew up in a very religious home, and through high school and college came into my own more nuanced perspective on faith and doubt and living in the productive tension between the two. And naturally this influenced my perspective on dating and sex.

I’ve been friends with a lovely person for the past year, and we starting dating a few weeks back knowing full well that after graduation (my undergrad, his grad) and our subsequent moves to opposite ends of the country, we’d return to being friends. I thought this would be something easy and fun (and it has been), but then I slept with him. Intellectually I know this was just a new experience, and I haven’t radically changed as a person, but it’s hard to resist falling into the shame and guilt that two decades of church teaching and abstinence sex ed associate with “losing” your virginity.

I don’t think God loves me any less now, or that my value as a human being has decreased, but I’m afraid that now I won’t ever be able to date someone with similar love for God and others. Basically that since this has happened, I’m no longer the good girl and shouldn’t expect to men with upstanding morals and character to have anything to do with me. Do you have any advice for overcoming this feeling of being damaged goods?

Unfortunately, many of the people in my life would think I should feel ashamed and repentant, and so I don’t know who to talk to. Bad enough not waiting till marriage, I didn’t even wait for a long term relationship with someone who says he loves me. I don’t regret it—he’s caring and kind—but I’m worried that one night may have ruined any chance at a happy long-term relationship down the road. How do I get over these irrational but deep-seated fears?

Good Girl Gone

DEAR GOOD GIRL GONE: First things first, GGG? You didn’t do anything wrong. You had sex with someone; this has absolutely nothing to do with your goodness or moral character. There’s nothing to feel ashamed of. Hell, all things considered, it sounds like you had a great first time. That, in and of itself, is something to be proud of. You were with a partner of your choosing, at a time of your choosing and on your terms, with someone who cared for you and was gentle with you. That sounds like a giant “win” to me. That’s the sort of triumphant experience that coming-of-age stories are written about

But now your jerk-brain is dripping poison in your ear and telling you that you’re “bad”, that you’re “sullied” and that nobody could possibly want you anymore. And I’m here to tell you: that’s bulls

t. Unmitigated, 100% pure bulls

t. You’re hearing the echoes of the lies that people have told you in order to control you, sexually and emotionally. It’s their way of trying to usurp your will and bend you to theirs, to tell you that you don’t have the right to make decisions for yourself. You’ve exercised your power and control and they don’t like that. So they tell you that you’re bad and that nobody of value could possibly love you now.

Bull. F

king. S

t.

Here’s what you need to know: people who judge you and shame you for how you lost your virginity are not people of upstanding moral character. People who tell you that you should be ashamed and repent have told you everything about themselves while knowing nothing about you. People who shame you, who browbeat you and denigrate you are not good people nor are they righteous or good, no matter what scriptural bulls

t they use to back up their slut-shaming ways. Even those who use “love the sinner but hate the sin” are looking for a way to judge people while still being superior. If we’re going to refer to the Bible, then let’s not forget that Jesus befriended, loved and defended the prostitutes, the thieves, the tax collectors, the beggars and the sick – the “sinners” – without shame or judgement. He accepted them as they were.

If someone judges you for having had sex, then they have shown themselves to be someone you don’t want to date. They have done you the favor of self-selecting out of your dating pool and good riddance to them; why would you want to date someone who thinks you’re damaged when you haven’t done anything wrong? Someone who shames you for having had sex can talk all they want about loving God and being a good Christian but their actions are proving otherwise.

(I’m also curious as to just how hard they’re having to lie to themselves about their future brides; less than 4% of adults are virgins on their wedding night, and I’d be very interested to know how many of those took advantage of God’s Little Loophole before the big day)

The only way that you’ve “ruined” any chance at a happy, long-term relationship is if you let these toxic beliefs control you and sabotage your potential happiness. A partner who is right for you is someone who loves you for you, accepts you for you and – critically – doesn’t see you as having done something wrong because you had sex when you chose to do so. Anyone who has a problem with that can f

k right the hell off.

Now I can tell you from experience: your jerk-brain is persuasive. It’s hard to ignore because it’s whispering in your voice and telling you all that all of your worst fears and anxieties are valid. But you can shut it down. Mindfulness meditation is especially good for taking control of your own brain; it teaches you how to control your thoughts and how to silence them when needed. It may also help to talk to somebody; contact The American Association of Sexuality Educators Counselors and Therapists and find a counselor in your area, or find a sex-positive therapist who can talk you through your issues. You may want to find a local church that’s part of a more accepting, sexually-positive denomination as well – the Unitarian-Universalist Church, for example.

But no matter what, I want you to remember: when you hear that toxic little voice telling you that you’re bad, that you’re sinful, remind yourself that it’s your jerk-brain and it’s full of lies. Remember that you’re an awesome person, someone who’s broken away from the toxic bulls

t that people have used to try to hold you down because they were afraid of you. You’re stronger than they were. You’re stronger than that voice.

You are powerful. You are good. And you don’t need to be ruled by other people’s poisonous beliefs and judgements.

Good luck.

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