DEAR DR. NERDLOVE: My boyfriend and I have been together for over six years. We’ve lived together for most of that time with my three children from a prior marriage. Our goal had always been marriage, as we had discussed it many times early on in our relationship, however over the years, it seems his fears grow and/or change.

He hates talking about feelings (his or mine) so we don’t get far in understanding his fears or addressing my insecurities. He has stated that he has trust issues from prior relationships, fears of divorce since he’s seen it all around him, that since I have been married before he doesn’t know if he can trust my stated feelings because I’ve felt that way previously. Plus, it just makes him uncomfortable to think about marriage and he doesn’t know why.

Now, other than his trust issues from a prior relationship, these reasons have just been added over time. Each year it’s something different on top of the prior trust issue. I find his reasons to be cop outs, honestly, but I’m trying to give him the time he needs to work his crap out. In the interim, as time passes, I can’t help but feel incredibly insecure that we have been together for 6+ years and he’s still not ready to fully commit to me. I have been clear on our goal from the beginning and haven’t veered off course. I want to be with this man and I want to spend the rest of my life with him.

I let him know consistently how I feel, and I reassure him in every possible way when he exhibits any insecurities about my feelings or my past. I ask if there is anything he wants or needs from me or the relationship and he states he has no issues and is happy with our life and wants to keep growing and moving forward. That all sounds great, but we aren’t moving in any direction. Our relationship is no closer to marriage then it was in year two. He states there isn’t anything I need to do or can do to help with his lingering trust issues, that it has nothing to do with me, but he also isn’t facing them on his own either.

I’ve considered that he just doesn’t want to marry me. He swears that’s not the case – that it’s not me, it’s just marriage. That’s hard to believe, because he was one that asked if I was jaded about marriage on our first date, because that’s something he wanted for his life. He gets angry when I call him out and say things like, “Just be honest and say you don’t want marriage so at least I can make the decision on my own whether or not that is okay with me.” He says he does want to marry me, he’s just not ready yet. I don’t want to pressure him into marriage, because I’m already insecure enough and don’t want to feel like he married me out of obligation. I want him to actually want to marry me.

I don’t know how to stay true to my feelings and on the path to the goal, while battling the insecurities that come along with this and not really knowing if my partner in this actually has the same goal. His messages are mixed and unfair. I don’t know the proper way to handle it. Any advice?

Always The Bridesmaid

DEAR ALWAYS THE BRIDESMAID: I have a lot of questions ATB, but most of them are for your boyfriend. Most of them come down to “dude, who are you trying to fool here?”

Literally none of his reasons make sense; the difference between being married and just shacking up isn’t so profound that it alters the very nature of your relationship. The excuses he gives you are almost transparently bulls

t, to the point that I wonder what’s going through his head. I mean “I can’t trust your feelings because you’ve been married before and it means you might divorce me”? I can’t decide if that’s absurdly naive or just profoundly insulting that he thinks you buy that as a legitimate excuse. Let’s be real: the fact that you two haven’t signed papers or had an expensive party isn’t going to act like a spell of Protection From Break-Up, 10′ Radius. He has trust issues, but they don’t seem to carry over into being willing to be in a long-term, exclusive relationship with you… just so long as nobody drops the “m” word.

Look, I’m not gonna lie here, ATB. This dude’s behavior is so squirrely that I’m wondering if he’s been storing nuts for winter in your attic. The fact that he keeps adding new layers to his “well I have trust issues” is something of a tell. The fact that he hates talking about feelings is another. So, for that matter, is the way that he keeps kicking the can down the road. “I’m not ready yet” is mightily convenient because it keeps you on the hook without actually committing to anything. It’s a way of placating you – we’ll get married someday – while he just makes sure that “someday” never actually comes. Now maybe this is because he’s just happy with the status quo of the relationship and he’s threatened by change. Maybe it’s because he actually wants to break up but can’t bring himself to pull the trigger and he’s trying to get you to do it instead.

But the only way you’re going to know is if you ask him.  You don’t need to be talking to some loudmouth with an advice column, you need to be talking to your boyfriend – and possibly a relationship counselor. If you want to get to the bottom of this, the two of you are going to have to sit down and have the extended dance remix version of The Awkward Conversation and figure out exactly where the lines are. He clearly doesn’t have a problem with having an LTR or even being a co-parent to your kids. Is it the word “married” that bothers him? Would he be ok if you referred to it as a “civil partnership”? Would he be cool if you two just nipped off to city hall, signed a couple pieces of paper that give you the legal rights of a married couple without making a big fuss about it?

But to be honest, I suspect that the conversation is going to go like this:

You: “Aren’t you happy to be in a relationship with me?”

Him: “Yup”

You: “And you like living with me and being part of my family.”

Him: “Yup”

You: “You don’t want to break up or be with somebody else.”

Him: “Yup.”

You: “And maybe you’d like having benefits like ‘next of kin’, being on my insurance and joint filing of taxes?”

Him: “That makes sense.”

You: “So would you like to get married?”

Him: “I don’t want to get married.”

So here’s what I suggest you do, ATB: you have to push your chips into the center of the table and make going to a relationship counselor a requirement of staying in a relationship with you. If he’s got trust issues and can’t communicate about his feelings with you, specifically, then it’s time to pull in a trained third party to help facilitate things. Hopefully then you can drill down to exactly where the hang-up is. If he can’t – or, more likely, won’t – then… well, I hate to say it, but you probably have your answer about where this relationship is going.

Good luck.

DEAR DR. NERDLOVE: I’m not really sure how to be attractive to women.

You’ve said before that a recurring problem you’ve seen in guys is that they refuse to change something that could be a tipping point for them and your stock response is ‘well, how is what you’re doing now working for ya’? I might be one of those guys.

I’m a college sophomore who has had zilch luck with the ladies, in college or otherwise. Recently, I think I’ve discovered part of my problem: that I’ve gotten so used to being below romantic notice that I have no clue how to be romantically noticeable.

I had a twinge of realization when I got back to school, having grown a beard over the summer, and got positive comments from both genders. But the realization fully hit me when I wore a yellow polo (I prefer wearing darker colors) and this really cute girl said I looked good in bright colors.

It got me thinking: maybe I should change things up. Put some more care into the beard, maybe change up my wardrobe some. I’ve made initiatives in the past to eliminate some creepy behavior, but I’ve come to the conclusion that while not being a creep is a good goal, thinking ‘alright, just don’t act like you’re a serial killer looking for his next victim, and you’re all good!’ is pretty low-hanging fruit.

Am I right? Am I a mile off the mark? Do you have any tips for beard maintenance? Am I going overboard because one girl gave me a compliment? Does this have some undertones on my psyche that I should know about?

I have many questions and not a lot of answers.

To Change or Not To Change

DEAR TO CHANGE OR NOT TO CHANGE: You are really overthink this, TCNTC. You’re right: “cool, you didn’t tell her that her skin would make an amazing lampshade” is pretty much the bottom rung of acceptable public behavior. The problem is that many, many dudes seem to think that this is all they need to do to and aren’t sure why they aren’t getting panties thrown at them left right and center. But like I’m always saying: you don’t get cookies for meeting minimum standards. That’s why we have things like The Grimes Test. (https://www.doctornerdlove.com/pass-grimes-test/)

But it’s literally everything else after that where you’re shooting yourself in the foot. I get that you’re worried about overdoing things or overreacting to one person’s opinion. But that’s not what you’re doing. It’s one thing if, say, somebody cute mentions that she likes the smell of one of the new Old Spice fragrances and you immediately go out and douse yourself to the point of being a walking mustard gas cloud. It’s another thing entirely when you’re accept some compliments about recent changes as positive reinforcement or signs that you’re on the right path.

Because that’s what happened here: you made some changes, got out of your comfort zone, fashion-wise, and lo and behold: people are sitting up and taking notice.

That is is what we in the relationship coaching business call “a good thing”.

Now I get it: change can be scary, especially when it comes to clothes. Our clothes are an outward expression of who we are – or who we want to be. When you’re used to dressing a particular way, changing it up can feel weird and unnatural. You can feel like you’re betraying your identity or trying to conform to somebody else’s ideas of who you’re supposed to be. But if it’s an organic choice, your exploring options that maybe you didn’t feel you had a right to try… well, there’s nothing wrong with that. You’re not giving up your individuality in exchange for shallow popularity or to appeal to the crowd, you’re just trying out some other ideas to see how they work.

And hey, it’s me saying this. If you watch my YouTube channel, you’d be forgiven for thinking I wear any colors other than black.

(And I do: there’s charcoal, midnight blue, dark navy…)

So take those compliments in the spirit that they’re intended, TCNTC. You’ve changed up your look and hey, you’re looking pretty good! I wouldn’t advise you to toss out your entire closet and start over with your new sartorial discoveries, but throwing some color into the mix is clearly a winner for you. Explore that a little more, find what works for you and what doesn’t and you’ll find the whole process to be organic and painless… with the added benefit that hey, folks are going to recognize that you’re actually pretty damn cute!

Oh and one more thing: if you’re going to rock a beard, then you need to take care of it. That means that you need to clean, comb and condition that sucker. I can’t tell you how many dudes lose attraction points because their beard looks like they stapled a badger pelt to their face. Keep it trimmed and neat – if you aren’t going to trim it yourself, then go to a barber and have them clean it up for you every other week or so. Use a beard oil to keep it soft and caress-able – personally, I like BeardBrand and a beard-specific wash to keep it looking and smelling nice. Trust me: bearddruf is a thing and it isn’t pleasant.

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 woman and my male friend and I have been friends for 8 years. For a few years we had fallen into a pattern of cuddling on my or his bed, something that made me uncomfortable, because I don’t really like cuddling, and I had told him that, but he didn’t seem to take it seriously and I didn’t know how to make him take it seriously. To be honest, I began dreading him coming over to my house or vice-versa. I had also told him about me being asexual, and had made no secret of my disinterest in a romantic relationship with anyone.

I noticed he was more invested in our relationship than I was, wanting to see me more, and also that he would get into a bad mood whenever I would make an allusion to my sexual orientation. So I was not that surprised when he told me he loved me last December. Since I don’t return his feelings, we have tried to remain friends, and I have taken the occasion to stop the cuddling and other uncomfortable touching (which was not easy since he tried to convince me we could continue).

Things are really tense between us. We were staying at a hotel with two of my (female) friends, and he got upset with me because he felt I ignored him, because I was talking to my friend and didn’t answer his question immediately. His attitude really put a damper on everyone’s mood that night, and my best friend stayed awake half the night because she was trying to stop my crying. He can also get upset because I don’t follow his advice. For example when I insisted on leaving a tip at a restaurant (with MY money), he told me “I already told you you don’t have to do that!” and when I started to defend myself, he walked away, after saying that I was the one making discussion impossible.

When we are with other friends of mine he often doesn’t talk at all, to the point I was relieved when he said he wouldn’t come to an outing, because I had been worried he would make things uncomfortable. He also often complains that he’s lonely and that I’m his only friend, which makes me ill at ease, and we had an argument about how I can’t take the stress of being his only emotional comfort.

The point is, I don’t feel comfortable with him anymore, but sometimes I feel like I am being too sensitive and looking for a reason to be upset with him, because things would be easier for me if I could just stop seeing him because he had offended me, so I would be ‘in the right’. But we have been friends for a long time, and I don’t actually want to hurt him, because he seems already in a bad place… My parents have pointed out I am often upset or irritated when I’ve just seen him, and I really don’t know what to do or if our friendship is worth saving, so could you share your thoughts on my situation?

I am grateful for your help,

Upset And Confused

DEAR UPSET AND CONFUSED: Um… I hate to say this UaC but you don’t have a friend. In fact, I’d go so far as to say you haven’t had one for quite some time. For the last several years, he’s been steadily pushing at your boundaries and trying to wear you down until you finally “admit” that you have feelings for him and that your asexuality is just some passing phase. Or perhaps he just wants to prove that he’s really the magic exception to your “not interested in sex or romantic relationships” stance.

Now maybe when you first started building from “acquaintances” to “friends”, it was genuine. You were a couple of cool, fun people who had things in common and really synched on an emotional level. You had fun hanging out together, sharing stories and experiences and becoming closer and more (platonically) intimate as friends do. Maybe as he got to know you better, he realized he couldn’t quite imagine life without you and was starting to realize that those warm and fuzzy feelings he felt when he thought about you weren’t quite so much in the head and chest level but were starting to spread to his groin as well.

But I kind of doubt it. While yes, there are plenty of friendships that turn sexual, there’s realizing that you’re into your buddy and then there’s “turning into a complete asshole who, incidentally, wants to fuck you.” Unless he got bit by a raging douchebag out on the moors, the odds are that this jackasserry was always there, just waiting to surface.

It’s like the old, traditional rhyme:

Even a man who is pure in heart/ and with female friends so tight/ may become a douchebag when the Red Pill flows / and bros are drinking Natty Lite

How we got to this place, however, is ultimately irrelevant to the more important question: “what do you do about it?”

And what you need to do – to borrow a line from NerdLove celebrity patronus Dan Savage – is dump the mother already. Yes, you can dump your friends, and in this case you totally need to. This guy is so toxic, we should change his name to Iocane Powder. I mean, the fact that he makes you miserable and drains the life away from you is really all the reason you need to ditch him; life is too short to spend it with people who make you miserable (although they make it seem long as hell…) But right now you’re hemming and hawwing because you’re falling victim to a mindset that society has drilled into so many women: you’re putting his possible discomfort at being dumped over the actual misery he’s causing you.

Let’s tally things up a little, shall we? He doesn’t respect (or want to acknowledge) your sexual orientation because it conflicts with his desires to get in your pants. He pressures you into activities you find uncomfortable at best and skin-crawlingly unpleasant at worst – because your wishes conflict with his desires to have access to your body in what is – let’s be honest here – a sexually charged scenario for him. He acts like a spoiled brat when he doesn’t get his way or if you dare to give someone, anyone else your attention and makes everyone miserable in the process. You are continually looking for reasons not to spend time with him because of how upset he makes you.

Why in pluperfect hell are you still talking to this guy?

No, your friendship isn’t worth saving… because quite frankly there is no friendship here. He is not being your friend by any stretch of the imagination.

It’s a shame he’s in a bad place (and holy shit is that putting things mildly) – but that doesn’t give him free reign to completely ignore  I’m sorry that he feels lonely (actually, no I’m not…) and that he only has you. The fact that he’s lonesome doesn’t excuse him from being an asshole. Hell, I’d go so far as to say that his shitty behavior and attitude is why you’re his only friend – you’re the only person who’ll put up with him. The fact that you’re his only source of emotional support doesn’t mean that his desires trump your boundaries. He’s being an entitled little shit who doesn’t acknowledge – or even care – how his behavior is affecting you.

I get that you’re worried about him and how he’ll feel when you tell him to get lost. While that iscommendable, it’s also more consideration than he’s giving your feelings. It’ll suck for him to lose his only source of emotional support, but perhaps he should be looking inwards as to why people don’t want to spend time with him.

Quit seeing him, quit spending time with him, quit taking his calls. You’re not obligated to explain why. If you do, make it clear that this is a download, not a conversation; you’re not asking for his input, you’re telling him what he did and why you’re out.

He’s toxic and he’s using you.

Dump his ass already. You’ll be much, much happier.

DEAR DR. NERDLOVE: A while ago, I wrote a letter to you for Ask Dr NerdLove about disclosing mental illness whilst dating. I just wanted to write back to you to thank you for your response and that your advice led to a happy ending!

Shortly after reading your response I developed the confidence to begin talking to an amazing woman online, where I disclosed about having CPTSD before our first date. Fortunately, she has been incredibly supportive and caring about it, whilst also giving her space to be able to talk about her own struggles and support each other. Long story short, ever since the first date we’ve developed an intense yet beautiful connection and are now ready to begin what is for both of us our first, serious relationship, which is something I’m incredibly grateful and excited to experience. I just wanted to say thank you dude for giving me the advice I needed, leading me to meet and fall in love with such an incredible person that back when I wrote the first letter, I would have never envisioned meeting. You’re a good dude and if I ever see you in person, I will make sure to give you a big hug to express my gratitude!

Thanks man and all the best,

Sandy Ravage

DEAR SANDY RAVAGE: That’s awesome, man! Congratulations and I’m thrilled to hear that things are going so well! Keep up the amazing progress and here’s to 2019 being an even better year for you.

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 going to make this a bit of a short story, starting with the present, moving on to the past, and ending with some questions on how to approach my love-life's future, if you don't mind.

I'm a 32 year old web applications programmer, and I have had no real experience with love, sex, or even dating. There's optimistic phrases for people like me, such as "late bloomer," or "don't compare your life to others, just live your life and things will be fine." But, I'm real scared that I'm on my way to being Steve Carell's 40-year-old Virgin. This leads me to not talk much about my love life with friends or family, but also, I think, leads to a circular problem because by not putting myself out there as willing or available, nothing really comes my way; kind of like job hunting. Compounding it all is the fact that I do suffer from some depression and social anxiety, which makes it tough for me to get out on my own. Leading me to go out only when I have friends or family available, and typically keeps me from going to or participating in things where I might meet other singles like myself.

Now for the past: I moved from a tiny town in a very rural area--like literally it was a 2 and a half hour drive just to go to a Walmart--when I was in the middle of High School to a larger city/metro with close to 3 million people. Made it hard to make and keep close friends. No real complaints. I've lived a good life. My Senior year of High School, I was a foreign exchange student in Kyoto, Japan, and went to a college prep (and English language friendly) school affiliated with the University of Kyoto. Met some friends that I currently pen pal (email) with today. Also, in my Junior year of High School, I was in Taekwondo. You would think a 16 year old boy would be hormone filled and super open to sex, but when a 26 year old instructor came onto me when we traveled together to a tournament with an overnight stay, I freaked out and was scared. Not really something you talk with any friends about, it's just embarrassing. In college, I kinda sorta dated this girl that was in several of my classes, but, honestly, and embarrassingly, I didn't really know how to take things a step further than just hanging out every now and then, going to a few movies, dinners, coffee shops, she even invited me over and cooked dinner a few times. I knew she wanted to "officially" date and was waiting for me to do something more...I could just feel it. But, I didn't know what to do, and didn't know how to communicate my feelings. I liked her, and wanted to take it further, too, but just wasn't sure how to get past where we were. So, we graduated, she moved for a job, I moved for grad school, and that was that. We kept up a bit from a distance over the phone and email, but not much anymore; she's married now. Got a scholarship to study at Cambridge in the UK for my masters degree. School was pretty intense, and I didn't have a whole lot of time. Weirdly, there was a guy that I shared a very similar experience with that I had with my "kinda sorta girlfriend" in college. We actually kind of dated, I think. And, if I'm honest, I was attracted. And, I think it was a similar situation where we just weren't sure how to go to the next step. So, I'm not really sure, but I may be bisexual.

That's where we get to where I'm at now, and how do I move forward. I'm back where I've been since I was a Sophomore in High School. Living alone, but about a half hour drive from the parents. Working as a programmer. Having a hard time getting out on my own. And, also a little confused about my sexuality because, let's be honest, I really have no real experience at all. How to a reconcile this and move forward. At 32, even if I'm comfortable with the fact that all my friends are married or seriously dating and I am doing nothing of the sort (which, I'm not), I feel like it's time to move forward a bit. It's hard to live alone at this point and not feel a little lonely. Any advice on steps to take to just get a catalyst going toward moving out of stagnation?

Thanks, Doc!

Too-Late Bloomer

DEAR TOO-LATE BLOOMER: It's interesting that you bring up The 40 Year Old Virgin, TLB. I've got a lot of issues with that movie - ranging from a casual approval of hooking up with someone who's too drunk to consent, complete with "nope, you have her" scene, to the equating sex with maturity - but there's a point a lot of folks miss. Steve Carell's character Andy has a pretty good life. Hell, aside from his lack of relationship experience, his life is downright enviable. He's got friends who care about him, a good job and - critically - he's actually appealing to women. His biggest problem is his own anxiety over sex and women. Once he starts to get over the label of being a virgin and starts just relaxing around women (especially someone as cool as Catherine Keener) he actually does really well for himself.

There's a lesson in there. Just sayin'. 

So let's talk a little about you, shall we? Because it seems to me that you're getting hung up on the big V label and ignoring the fact that you've got a lot of things going for you. I mean, you went to good schools, you studied overseas, you practice martial arts and oh hey, YOU GOT ACCEPTED TO CAMBRIDGE. 

That's pretty goddamn impressive TLB. A lot of folks would tell you that this alone is a pretty impressive list of things that make you interesting and a potentially great partner to women.

But what about the downsides that you list? You live in the city where you went to high-school. OK and? It's a decently sized down, which means that you don't have the demographics problem that folks in small towns frequently run into. You live half an hour from your parents. And? Living in proximity to your folks is hardly a bad thing, especially if you're close with them. Hell, even living with them isn't that big of a deal - not in this economy. But you've got your own home, a good job, folks who were into you, good friends... 

Ok, maybe that 40 Year Old Virgin comparison was more apt than you realize.

Your biggest problem is your anxiety around sex,  being a virgin and your lack of experience. And while I realize you feel like you're The Last American Virgin, I promise you: you are not alone in your lack of experience. There're lots of folks who are in the same boat as you, with the same anxieties. And I'll tell you what I've told them: 90% of that anxiety is bulls

t. Whether or not you've had sex doesn't say anything about you as a person. It doesn't say anything about your worth as an individual, about your desirability, your maturity or your masculinity. It's just one experience you haven't had yet. And you will.

Now with all that having been said: in your case, some of that anxiety is earned. I mean the fact that your adult instructor hit on you when you were 16 is super-goddamn inappropriate. I realize that there's a lot of cultural bulls

t around boys being horny by definition and "wouldn't it be awesome" stories around teachers banging students but holy hopping sheep-s

t NO IT WOULDN'T. That's the definition of someone in power abusing their authority over someone. You shouldn't be embarrassed about freaking out over this, that's an entirely reasonable goddamn reaction... especially when you're travelling and have no way of getting out of their on your own. It's good that nothing actually happened, but the fact that you're treating this as a failure on your part is messing with your head.

That's my my first suggestion would be for you to talk to a counselor. Working with someone to untangle the whammy you've got on your head around sex is a good start. But so is working on any issues you may be having with depression or social anxiety. That alone is going to do a world of good for your mental health and self-esteem; the more you get that under control, the easier the rest will be.

My second suggestion would be to stop focusing on what you don't have and look at what you do have. Now I realize this seems a little flippant, but there's actually a point to it. Practicing gratitude is a key part of not just learning to be happy, but also building your sense of confidence.  Making a list of things that you're grateful for and expressing that gratitude is surprisingly powerful. It strengthens your relationships with other people, it helps change your perspective on your own life and, honestly, it makes you feel better. Recognizing that you have more going for you than you realize is a great way to help boost your sense of self-esteem and develop the courage you need to take the next step in your relationships.

Which brings me to my third suggestion. The biggest issue you're facing when it comes to your relationships is that you just need to muscle up and take a leap. If you want to take things further, then all you need to do is open your mouth and make the words come out. They don't need to be smooth or perfect. Hell, being nervous would probably increase your appeal with many women; there's a reason why "adorkable" is a thing, after all. But all it really takes is to say "hey, I like you and I'd like to take you out on an actual date." So my advice for you is to not wait for a catalyst, it's to be the catalyst you need. You are the lever you need to lift yourself out of this rut. All you need to do is commit to putting yourself out there and actually making that leap when you're with someone you like.

You don't need to make a production out of it. You don't need to tell them you have feelings for them. All you need to do is say "I'd like to take you out on a date" — preferably with a specific activity at a specific time in mind. The feelings are implied by the fact that you want to, y'know, go on a date with them.

Yeah, it can be scary. Yeah, it opens you up to the possibility of rejection. Do it anyway. Let your knees shake and your heart pound and your voice break, but do it anyway. Take chances. Explore possibilities with people you're attracted to, regardless of their gender. Let yourself make mistakes, learn from them, get back up, dust yourself off and try again.

Commit to making these changes in your life and I promise: the rest will take care of itself. 

You've got this.

All will be well.

DEAR DR. NERDLOVE: I know it seems like a self-explanatory question, but hear me out. I went on a date with this cool dude last week (met online), and thought it went really well. We seemed to hit it off? My anxiety comes from a few things:

1. It's the holiday season so I'm not sure how much additional busy this adds vs regular "too busy to hang out"

2. I've never been on a date with someone I'm not in a relationship with, so I have no idea what to expect afterwards

3. He doesn't seem to be the best at communicating his thoughts on emotional stuff

Soooo he says he'd like to hang out again but I keep getting "not in the next [time period] because busy" (I've only asked twice, and he was able to meet right away for the first date). But also it's holidays so... ?

We continue to send multi-message responses to each other when we have time to answer.

(Another thing I feel a little weird about: he was watching the time so he could get to bed for work the next day, but I lost track of time because I was having fun. Not sure if this is just a personality difference or what but I'm overthinking everything and it's making me anxious and I think I just need some perspective from a more experienced party thank you so much for reading this messy wall of text I love you like a sister)

Halp

-Confused First Date

DEAR CONFUSED FIRST DATE: First, let's handle the timing question. As someone who's neurotic to the point of anxiety about how much sleep he gets, having a hard limit so he can get up in the morning is entirely reasonable to me. Assuming he's being honest with you - and we should give folks the benefit of the doubt on a first date - then that's just a personality difference. Don't stress too much about this unless it comes up again.

But for judging how the date went? Well, that's where things get tricky.

Here's the fun - for suitably frustrating definitions of "fun" - part about dating: because people have this annoying tendency to be individuals, it's kind of impossible to say exactly what you should "expect" after a date. There are people who will want to go on another date right away. There're also people who will be afraid of being too eager if they do so, so they'll try to create some artificial scarcity. Some people are legitimately busy and have a hard time fitting relationships into their lives, while others are off in their own little world and rapidly running out of oxygen.

So you can't really give a one-size-fits-all answer to how to tell whether a date went well or what you should be expecting afterwards. But there is one thing I've found to be true: if someone wants to see you again, they'll let you know. Even if life gets in the way. Even if they're not necessarily the clearest and best communicator out there.

Right now, it sounds like your would-be beau is being real with you. Between all the various winter holidays, New Year's and even a little of the weirdness that comes with dating around Valentine's Day... yeah, it gets hard to find time to breathe never mind date. So here's my suggestion. You know he's busy for the next [time period]. Find out when said period ends, then make plans for the following weekend. Name a specific activity on a specific day and time. "Hey, I saw there's $COOL_THING happening on $THIS_DATE and I'd love to go to that with you. How does that sound?"  People are more likely to say yes to a specific time and activity than they are to "go out some time next week". Specificity helps because he's now able to check his schedule and - if he's free - keep that day clear for the two of you. It's easier to say "I can't do X on Saturday" if he has a date planned. If it's more nebulous, it's easier for life to seep in and steal his availability.

But if he can't make it? Then see how he responds. Does he say "Ok, I can't on Saturday, but I've got Wednesday free. How does that work?" Or does he give a "I can't, I'm gonna be busy that day" with no alternate suggestions? If it's the former... well, that's a pretty good sign that he wants to see you again. If it's the latter, then either he's not interested, or he can't be bothered with taking the initiative. And in that case, you have to decide whether you want to keep trying, or if you want to be the person who's going to have to do all the planning. 

And as a general rule of thumb: one "I can't, I'm busy" is happenstance. Twice is coincidence. Three times is enemy action. Wait, that came out wrong. Three times is a message. And that message is "I'm not interested." 

Good luck.

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