DEAR DR. NERDLOVE: I could use a bit of advice. There is this girl that I had a crush on in high-school, and I am pretty sure she reciprocated it. I didn’t do anything at the time for a variety of reasons, chiefly I was being a coward. I take a bit of solace in that I would have been a crappy boyfriend at the time, and have since become a better man and better in relationships. Anyway, not doing anything is my biggest regret to date that anything can be done about. She lives a couple hours away from me now, and as far as I can tell she is single. I don’t have her number or email address anymore, but I can message her on Facebook.

I would like your advice on whether or not I should reach out to try and reconnect. I don’t want to come off as a creeper. I was thinking of reaching out to reconnect and invite her to coffee the next time she is in town (she still has family where I am). I figure I shouldn’t lay it all on the line saying that I regret not asking her out 8ish years ago. That seems kind of creepy.

Regardless of what I say, even if it doesn’t go my way, it won’t be that bad. The absolute worst that could happen is she thinks I am a huge creeper and says so to all of our old mutual friends and they have a laugh. I’ve lost touch with most of them, so no skin off my back. The best that could happen is we have coffee or whatever and things go well and they lead to a relationship.

So, I guess what I am asking is should I reach out or am I being an idiot? If I should reach out, should I avoid laying it all on the line? I could use some brutal honesty here. That is why I like you advice articles, you don’t pussy-foot around.

Second Time Around

DEAR SECOND TIME AROUND: So I have a question, STA: it’s been eight years… why are you still hung up on this woman? Eight years is a long goddamn time to hold on to a high-school crush, especially when you’ve been completely out of touch.

Don’t get me wrong, I can totally understand the feelings of frustration when you’re dealing with someone you see as The One Who Got Away but at this point, do you really even know who she is any more? You’re not the same person you were back in high-school… so why do you think she’s the same person you had a crush on? I think it might do you some good to ask yourself whether you’re still into her for herself or because of what she represents. Chasing after someone who’s more symbol than person – your unicorn, your white whale, whatever – isn’t fair to her and it’s incredibly disrespectful; she’s a person, not a fantasy, y’know? And it’s not good for your personal development to hang on to all of those missed opportunities; when you’re stuck looking back at all of those might-have-beens and woulda-coulda-shoulda moments, you end up missing out on the opportunities that you do have.

Now, does this mean that you shouldn’t send her a friend request on Facebook and see if she’s interested in reconnecting? Not necessarily. Facebook has basically become the replacement for the high-school reunion and it’s not weird to want to reconnect with people you knew. But I think you need to be careful and you need to be realistic. The odds are that you probably aren’t going to get together and in your current state of mind, it’d be a mistake to try. Some regrets are better left as regrets and allowed to fade with time. You want brutal honesty, I’m going to be brutally honest: I don’t think this is the greatest idea. But I also think you’re less asking me for advice and more for permission for something you want to do anyway. So with that in mind:

If you’re going to reconnect with her, don’t do it with the intentions of trying to correct your mistake from all those years ago. Treat this as simply trying to connect with someone new. Get to know who she is now, rather than who she used to be. Learn to see her a a person instead of the fantasy you’ve had rolling around in your head for the past eight years. Get coffee if she’s amenable to it. Do not lay out that you’ve been dying to ask her out since high-school; you’re right, dumping all of that on her would be incredibly f

king creepy. Simply play catch up. No dates. No hooking up. No even hinting at it. No being Mr. Nice Guy and trying to backdoor your way into a relationship with her.

If – and I’m going to need you to be brutally honest with yourself – you’re able to let go of that fantasy and connect with her as a person – then you can bring up that you had a crush on her. “You know, it’s crazy and I can’t believe I’m saying this but when we were in high-school, I had the hugest crush on you and I have to admit, I’m kind of disappointed that I never managed to ask you out.” And then leave it at that; something crazy that happened in high-school. But you’re not in high-school any more and neither is she. Let the fantasy go and maybe, just maybe, you might find a genuine friendship with the person underneath.

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’m in a rut. The most serious relationship I’ve had to date ended in late January, 2014. It lasted just shy of two and a half years. It’s now December 2014 and I can’t move on. I started the relationship as an out and proud gay man. I started the relationship the same way, but what I thought was love wasn’t – I was dating someone who was still in the closet, needed space to “find himself” and he found himself with five other men (maybe more?!) in the time we were together.

It killed me because I thought I was being supportive, understanding, nurturing, and caring. In the end, I feel like I was made the butt of a big joke. He moved on and was in a relationship less than a month later, and while it’s an immature move, they exchanged promise rings over Christmas. Now, I’m 30, my ex is 28, and his new boyfriend is mid-twenties, so I think the promise ring thing is an immature move, but it still stung in it’s own way. When we were together we had a lot of “hey, I’m not ready to share this relationship with so-and-so” moments where I stood by with support. It hurts that now someone else is getting the “out and proud” boyfriend I was asked to support and wait for.

Where I used to be “out and proud” of who I am, I’ve begun to have some serious self-doubt and question my self-worth. The fear of feeling duped again is leaving me stunted in singledom.

How do I get back on the unicorn now that I’ve fallen off?

-Slightly-Dimmed Rainbow

DEAR SLIGHTLY-DIMMED RAINBOW: Ouch, SDR. It really sucks when you find out that you find out the person you thought they were – especially when it leaves you feeling like it’s some how your fault that things didn’t work out. You’ve put in all this effort, all of this concern, all of this emotion… and now you’re left feeling like you were a stepping stone to your ex’s “real” relationship.

Worse: the fact that he was able to move on so quickly, so easily makes you question everything about the relationship. Where you not good enough? Was there something you could’ve done differently? Why weren’t you enough for him?

But hey, you’ve written to me because you want the answers and fortunately, I have one for you: the problem in your relationship is that your ex was an a

hole. You were being used and manipulated by someone who took your honest affection and pissed all over it from the get go.

So up front: as a hetero guy, I’m not going to have the same experience and perspective as a gay man about being closeted or not. There’re nuances and realities that are outside of my lived experience, so take my opinions with suitable levels of salt… but frankly, your ex sounds like he was using his being closeted as an excuse. Maybe he wasn’t secure enough in his sexuality to be openly dating someone – hence the constant rules “hey, let’s not tell X, Y and Z that we’re dating” – but he sure as s

t had no problem f

king them on the down-low. Now maybe it took time for him to finally be willing to be open and out and proud. Maybe he needed time to mature and come to terms with himself.

But that doesn’t excuse the fact he was a toxic a

hole who treated you like s

t. And to be perfectly honest, I think there was no small part of him that was using his being closeted as a way of having his cake and f

king it too. After all, if you’re just Schrödinger’s Boyfriend – officially together when he wants you, less so when he decides he wants someone else – there’s that level of deniability when he’s off “finding himself” in someone else. By saying “I’n not ready to share this relationship with X, Y and Z”, he was telling you that he had reasons that he didn’t want people to know you were dating… and I suspect he also used this as a reason why you shouldn’t be around when he was off with other guys. I wonder how many of his other partners might have balked if they knew that he was with someone else.

So you weren’t a joke, but you were unfairly used. The most generous interpretation I have is that you were basically his practice run at a relationship. The less kind says that he’s a s

tty end of the stick and it was completely unfair to you.

So what do you do now? Well, the first thing you need to do is put this guy in your rear view mirror. He’s an a

tty manipulator, a toxic user who dated you in bad faith, who took advantage of your sincere affection to fulfill his needs until he was ready to come out. Either way: you got the s

hole who treated you badly and the last thing you should be doing is using him as your metric of comparison about your worth as a person. It hurts to watch someone you cared for withhold affection from you and then turn around and shower it on someone else but trust me: you dodged a bullet. Blessings in disguise aren’t fun and right now you’re in a lot of pain but in the future, you’re going to look back on this and realize how lucky you were that this relationship ended when it did and how much you learned from it.

And that’s what you need to do: take what you’ve learned about users and manipulators and apply it to your future relationships. Maintain some strong boundaries, especially in the early days when you’re just starting to get to know people and you’ll weed out the majority of users, game players and toxic people.

Meanwhile: cut this guy out of your life. You don’t need to constantly be reopening the wounds he gave you by watching him play relationship with someone else. Take the nuclear option and spend some time recovering from this relationship so that you can let your heart heal. You’ll find someone else, someone infinitely better. And when you do, you’ll be glad that you don’t have this guy in your life any more.

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: Watched a few of your videos but am still in need of more advice. Long story short my love life is non existent, I’m a failure at dating, I’ve got next to no experience and I don’t don’t know how to fix this. In fact while I see my friends meeting people, falling in love, marrying etc I myself seem to be getting worse: I’ve gone from being rubbish at relationships/dating to barely being able to talk to a girl I’m interested in.

My friends tell my I have loads to offer and if I think logically I can see that: I’m told I’m not bad looking, I’m in decent shape, I’m financially stable and have my childhood dream job (firefighter) which I enjoy and I am passionate about. I have a variety of hobbies and interests that I frequently travel the world to pursue. My social circle is small but geographically spread out so my social activities are infrequent therefore I prefer smaller social gatherings and it takes me a while to warm to people socially but I’m told once I do I can be very interesting, funny and appealing. For some reason as soon as I meet someone I am interested in romantically I forget all that stuff, I get nervous, become consumed by the idea that they are ‘out of my league’ and I am just inconveniencing their day and it spirals from there. I don’t buy in to this idea that dating is about playing games with people but I do think you need to know how to date to succeed and I simply don’t know how. Suffering failure after failure, rejection after rejection my confidence is shot to pieces and I’m now terrified of approaching people.

The truth is I am happy with my life, my work and my hobbies but I would so very much like to share it with someone and I’m genuinely terrified of the idea that I might never meet that someone. My job sees me regularly dealing with people in their hour of need. I love being able to help these people but with it I see a lot of death and a lot of people who have died alone or live isolated and lonely; sometimes I can’t help but wonder if I’m seeing my own future.

I’d really like to do something about it and I realize the only person who can do that for me is me, but I need someone to advise me what I can do and where do I start?

Lost and Lonely

DEAR LOST AND LONELY: Here’s a secret, L&L: there is literally no difference between the people you’re friends with and the people you’re attracted to. The only thing that divides the two — the thing that’s causing you to stress out, forget about all the amazing things you bring to the table and forget that you’re a hell of a catch — is in your head.

I mean, come on: you’re a firefighter. Your job is to charge headlong into danger, to literally go where brave men fear to tread. That alone is going to be catnip to many, many women. Being brave and selfless, throwing your very body into peril for the sake of others? Even if we discounted the rest of your amazing qualities, that alone is going to make many people take one look and say “Hellooooo salty goodness.”

But you don’t believe that.

The reason why you’re so at ease with the people you’re friends with is because you don’t put the importance on them that you put on people you’re into. While you clearly care about them and you want them to think the best of you, you aren’t measuring your worth by your friendship with them. You don’t see being friends as a sign of your value as a man or as a lover, therefor you’re able to let your guard down and just relax around them. To quote the bard: there is no good or bad but that thinking makes it so.

That all changes as soon as you’re confronted by the possibility of dating someone. Now you’re feeling like it’s all on the line. Despite the fact that you are a goddamn real life superhero, you feel like you don’t have any inherent value that other people could possibly relate to and so now you have to be absolutely perfect, otherwise nobody could ever love you. And when you get rejected then it just becomes further reinforcement of the idea that you’re worthless and that you’re doomed to die alone, unloved and unmourned.

But here’s another secret: everyone gets rejected. Nobody goes five for five. It doesn’t matter how hot, rich or famous some guy is, there are women out there who wouldn’t f

k them with a borrowed vagina and 90s Brandon Frasier doing the pushing. I have watched as celebrities — people you would recognize if I told you their names — got shot down in front of me. Hell, I’ve had friends who’ve told certain individuals who were in the running for Sexiest Man Alive to piss off and leave them alone.

What you need, more than anything else, is to develop a case of the f

k-its. She seems like she’s out of your league? F

k it, she may be amazing but  there are literally millions of other women out there who are just as amazing as her, if not moreso. All that she’s done is confirm that the two of you simply weren’t compatible. And if that’s the case? F

k it, there’s no point in worrying about her; you now know that you two were never going to work and you’re free to go find someone who is right for you.

Here is a third secret: most of the time, you’ll be rejected for things that have absolutely nothing to do with you. She may be in love with someone else. She may have just ended a relationship and isn’t ready to start dating again. You may look too much like her asshole ex and she’ll never be able to overlook that. You approached her when she had an awful day at work and she just couldn’t today. You never know because you’re not her and the only reason why you assume it’s you and not her is because you live 24/7 in your own head, therefor you naturally assume it’s your fault. But you can’t know that.

So f

k it, you’ve got tons to offer, and she’d be crazy not to be into you. She turned you down? F

k it.

The more you’re able to decouple your assumptions about what other people think from your estimation of your own value, the less you’ll fear rejection. This doesn’t mean that rejection won’t hurt — it always stings when someone we’re attracted to isn’t attracted to us in return — but it won’t destroy you, either. It’ll just mean that you’re one step closer to finding someone who’s right for you and who gets just how goddamn awesome you are.

All that stands between you and some astounding dating success is adjusting how you see the world and learning to accept that you are a sexy bad-ass, a goddamn sexual tyrannosaurus who’s being held back by the thinnest thread of gossamer. Once you can make that mental shift and believe in yourself and your own worth? You’re going to be amazing.

So, y’know. F

k it.

You’ve got this, L&L.

Good luck.

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