DEAR DR. NERDLOVE: So right before the COVID lockdown I was building up some courage to ask out a lady I saw pretty lady at a regular social gathering with friends. Didn’t want to ask out in a text because that felt lame, but there were always just enough other people around that asking out felt like it would’ve put her on the spot. Then COVID happened and the group stopped meeting in general, and since she’s not on Facebook I have no real idea what her current life situation is. 

Is texting out of the blue to see if she’d be interested in a date after basically an entire lustrum rude, and as lame as I thought it was back then?

Five Years Too Late

DEAR FIVE YEARS TOO LATE: OK there’re two very different questions embedded in this letter, FYTL. Let’s start with the easiest one: is it rude to ask someone on a date out of the blue, five years after the last time you’ve spoken? Kinda, yeah. Will it work? Hell no.

I think anyone who gets that text is going to be bewildered, possibly needing a moment to process why, after five years of radio silence, you’re messaging her now and saying “hey, want to go on a date” without so much as a “hi, how are you, long time, what’s been going on?”

And that’s if she even remembers or has your number in her phone. She may well think you’re another spam text trying to lure her into a pig-butchering scheme if she doesn’t just scratch her head and report the text as junk.

If you were going to try to ask her out, you’d really need to spend time to re-establish a relationship with her. And I mean a lot of time. Five years of no contact is a very long time to go without speaking. Expecting to pick up where you left off is wildly optimistic at best. Yes, there are some folks out there who don’t have what one might call a “friendship degradation mechanic”, who re-engage with friendships like no time has passed… but you really can’t rely on her to be one of those people.

This is why I’m a big believer that you can’t wait for “the right time”. You make the right time happen, or else you accept the higher risk that you’re going to miss out.

Now as to your second question: is asking someone out by text lame? Not really, with caveats.

This is the 21st century; most of our communication is done via text and our thumbs. We live our lives – for good or for ill – on networks and computers and screens as well as in the physical world. Entire relationships are conducted and managed via text, DMs, email and voice chat in video games. So in and of itself, no asking someone out by text isn’t lame.

Now that being said, if you weren’t texting her already and that’s your first message to her, ever? Yeah, that’s going to seem a bit weird. It could be a bit understandable if you two were talking regularly when you saw each other and you could never find a time when you could ask her out, but it’d still seem a bit odd.

But if you weren’t even talking to her at all – not beyond basic niceties and small talk, the “know each other well enough to say hello to” kind of conversations? Yeah that’s going to seem kinda lame and more than a little clueless.

With all that in mind, let me give you a little tip for next time: when you’re hoping to ask someone out on a date, your choices aren’t limited to “ask her out furtively in secret “ask her out by text” or “put her on the spot in front of God and everybody”. You can get a sort of effective privacy without actually pulling her away into the trees where nobody can see.

What you do is use a combination of physical distance and body positioning. You get a bit of distance from the larger group – not much, but enough so that you’re not standing in the middle of a crowd, just a bit off to the side. You’re still within eye and earshot – hell you may be just outside of arm’s reach – but it gives a bit of psychological distance that’s greater than the physical distance. Then you position yourselves so that her back is to the group while she’s facing you.

Doing this creates a sort of privacy bubble; you’re not actually away from everyone else but you’re clearly having your own conversation that doesn’t involve the others. Not having the feeling that all eyes are on her or paying attention to what you or she are talking about creates the feeling that this is a private conversation even though it’s still right there. And then you have your opportunity to say “hey, there’s $COOL_THING going on this weekend and I think you’d really enjoy it. I’d love to take you if you’re interested” without you or her feeling like she’s being put on the spot.

Just as importantly though, you need to work on not treating asking someone out on a date like it’s a shameful or weird thing. It’s all a lot easier when you don’t act like you’re doing this risky thing or making a huge ask when all you’re really doing is saying “hey, I like you, I’d like to spend time with you, would you like to spend time with me?”

Get used to just owning being interested in taking someone on a date without fear or shame, and I think you’ll have a much better time. And you’ll hesitate far less and thus not spend five more years trying to figure out how to undo that mistake.

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: Some details may be changed or left ambiguous to maintain anonymity. A few weeks ago, after coming back from a vacation, I found myself choosing between two men. I met the first a few months ago. He was very sweet and a high-quality man. He checked the boxes. He was attractive physically. We got along well, and he was serious about his interest in me. We also aligned in terms of values. He immediately ingratiated himself into my life by attending my church every week and eating meals with my family. Before long he was receiving invites to join family functions. I enjoyed his company as the only young single person at these small gatherings otherwise, but I felt confused feelings for him. 

He had quirks. The major ones he stopped when I mentioned it, but there were still minor ones I noticed. They weren’t turnoffs or dealbreakers but I noticed. Also, our conversations didn’t seem to extend any deeper than causal friends who hung out a lot. I also didn’t feel anything when I held his hand on an ice-skating date. I didn’t find myself wanting to hold his hand either when he never grabbed it during a museum date. This museum date was after 4-5 months of talking. He never initiated anything physical over 6 months. He never even said good morning or good night to me over text, but he made it clear he was interested in trying to spend time with me, introducing me to his dad and friends, requests for exclusivity, and compliments. He kept things chill while I studied. I wanted to feel things, but I questioned whether I felt any chemistry. Perhaps he was holding back affection and intimacy because of my hesitation, but maybe I needed that to fall for him.

Towards the very beginning of seeing him, a friend reached out about a singles vacation. I agreed and went on it because it looked like fun. I was not really looking for anything because of my situation, but I met an attractive someone who lives in a nearby state, again with the same values. We did have a deeper emotional connection. I did feel attraction for him in person that I didn’t feel with the first guy. I’m sure this guy has quirks but I’m not seeing what I noticed in the first guy. So I cut things off with my guy friend when I came home. 

I, however, find myself surprisingly regretting it. The first guy doesn’t respond to me anymore. I miss texting him and sharing memes. He had been there for me while I was preparing for a big grad school test. He had also started trying to plan more romantic things like a riverwalk when I got back and a trip to meet more of his family. 

I find myself sad that I can’t do that with him. Sometimes I find myself wondering what if? What if I had talked to him about what I believe may have been a lack of emotional intimacy? Would that have caused me to have romantic feelings? What doesn’t help is that my now boyfriend lives in a different state. Everything is great there but I’m still thinking of the first guy. I can’t tell if I actually do have lingering feelings for the guy I ended things with or if I simply miss my friend’s companionship. Logically, I think I made the right choice, but I just want to see and talk to this guy again. I don’t know what to think or do. 

Thank you!

Somebody Make Up My Heart

DEAR SOMEBODY MAKE UP MY HEART: It’s hard to know what was going on with your first beau, SMUMH. Maybe he was somewhere on the asexual spectrum and just not necessarily someone who wanted or was comfortable with physical intimacy – not yet, or possibly not ever. Maybe he was one of those people who truly believed in no sex – or anything even approaching sex or triggering arousal – before commitment, an engagement or marriage.

Or maybe he liked you but wasn’t really feeling it either, not romantically. That doesn’t mean he didn’t want to feel it, mind you. But what sometimes will happen is that we’ll meet someone we like, who we feel like checks all the right boxes for us but they don’t quite do it. On paper they’re a great fit, but in person there’s just some missing x-factor that we can’t put our finger on and the lack just kind of lingers like Banquo’s ghost. There’s a desire to close that gap, to make that missing feeling happen and when that doesn’t work, we may round the feelings we do have up. We say “ok, that’s close enough.”

And it isn’t. It’s a good relationship… but it’s not romantic. It’s like a very demonstrative friendship. Possibly even an intimate one… but it’s not love. It’s not passionate.

The problem is that it is a good relationship. It’s just not the one that has what you need, the one that scratches that particular itch. But because it’s good, you don’t necessarily feel like you’re supposed to – allowed to, even – say “this is nice, but it’s not enough”. And so we often stay because we don’t have a reason to go, not one that we would think justifies leaving a perfectly functional relationship.

But it’s like I’m always saying: you’re allowed to leave a relationship at any time for any reason. And “it’s nice, but it’s not enough” is a very good reason. You can and should prioritize wanting the relationship that fulfills you in the ways you need, whether it’s emotional, sexual, whatever. And while it’s true that there’s no such thing as settling down without settling for, the whole point is that you’re getting so much from that relationship that you don’t miss what you are giving up in exchange. You’re pleased with that trade-off because the rest is worth it.

Saying “every relationship’s a compromise, I should get by without this” is a good way to end up in a relationship that leaves you feeling hollow, like you’ve wasted time. And I think you would’ve ended up the place you are now, just over a much longer period and possibly without another partner who matches you better than your first one did.

Now personally, I think you did the right thing. You had a friendship that you valued with this first man, but you weren’t getting what you needed for it to be more. Your second guy gives you those things and in this case, gives you enough that you’re ok making the sacrifice of having a long-distance relationship with him.

But it’s understandable that you are questioning things. I suspect that this is more because for six months you had a relationship that you truly enjoyed and valued and now it’s gone. The empty space where he was is haunting you because it’s a reminder of that lack. It’s a genuine loss, and it’s natural to regret that loss and wonder if there were some way that you could’ve prevented it – had your metaphorical cake and eaten it too. But I don’t think there really was, not the way things are now.

I’m also not surprised you don’t hear from him anymore. I’m sure he’s feeling hurt and confused. I suspect that, even if he wasn’t necessarily feeling it for you either, he wanted to and was making those larger bids and gestures in hopes that he was going to spark something. Or maybe he was feeling your hesitation and was trying to make it spark in you. Either way, it didn’t work and you ended things with him in order to be with another man. And that’s going to hurt. No matter how gently you break it to him, it’s not likely to be like you’re letting down James Marsden – a man apparently destined to be the dude who has to be cool with the heroine leaving him for someone else. You’re telling a guy who wanted to make things work that it was never going to happen and you found someone who could make it happen.

Even if he agreed with you, it’s still going to take time for him to process that hurt, come to terms with what happened and find enough healing that he can move forward.

But here’s what I would suggest for you. Take some time to do a bit of a mental exercise: how much longer in this relationship would you be willing to wait for those romantic feelings to spark? Would you be willing to wait another six months? A year? Two years? Five? If you knew that the rest of your relationship with him would be like this, working on the emotional intimacy and waiting for your feelings to kick in and never knowing when or if they would, how long would you be willing to endure this status quo?

Because here’s the thing: yes, love can grow over time, but you were at a stage in the relationship when that emotional and physical connection should be at its easiest, and it just wasn’t there. I suspect you had all the components you needed for a good, strong friendship, but not what you needed for love, no matter how much you or he wanted.

And that sucks. But sometimes that’s just how it is. I think you made the right decision for you and that’s really all you can do. Hopefully, with time and distance, your ex will be able to come back around and the two of you can have a friendship again… but this time you’ll know it for what it truly is. And then you will be able to have the best of both worlds, in a way that’s healthier and happier for everyone.

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 just want to start out by saying that I’ve been reading your blog posts and watching your YouTube videos for a while now, and your advice has really helped me a lot. With that said, I have a couple of questions:

The first question is if you think that I should keep going out to a casino near where I live to work on cold approaches. To clarify, I live in Las Vegas. I am currently leaning towards ending this practice. I don’t gamble. I avoid drinking when I can because of the health effects and the price (who wants to pay $20 for a cocktail?) I also don’t really like the noise, crowds, or staying up into the late evening hours (yes, I know I’m getting old). I mostly just make myself go on Friday or Saturday nights because I know getting out of the apartment will be good for me, there will usually be beautiful women present, and I can work on my cold approaches. In a way, I kind of think of it like a gym for social skills and game. On a side note, I think doing cold approaches works better when you are sober because you feel your fear more acutely. Anyways, I wanted to ask you if you thought it was worth continuing to go out to this place because I don’t particularly enjoy it and I am not exactly preselecting for a person who would be compatible with me.

The second question is about sex – specifically, when you should begin having sex when starting a relationship. I come from a pretty conservative background that taught me that sex before marriage was a grievous offense, but I’ve since come to believe that it’s just a fun recreational activity that you and your partner can both enjoy, provided there’s consent and mutual trust and respect involved.

The reason I ask this is that, well, I’m a typical guy, and I’d love to start having sex as soon as possible. However, I know a lot of women take time to develop trust, which it totally understandable. They also don’t want to be slut-shamed for being too quick to jump into the sack. The other part of this is commitment; a lot of people say that sex should require commitment, and I see their point: it’s the quite likely the most vulnerable position a person could possibly be in, especially for women. I’m just asking because I want to develop a good ethical position that rests upon solid principles. I also don’t know when it’s appropriate to broach the subject or express an interest in having sex, since asking for sex too early gives the impression that I “just want sex.”

The third question also pertains to sex. This may strike you as an odd question, but do you believe celibacy is a good motivational tool for making approaches? On the one hand, I feel like porn and masturbation just sap my motivation to approach women that I’m interested in. I’m concerned that porn hijacks a very powerful, ancient reward circuit and delivers nothing in return. To be honest, if I wanted to do only what felt easy or comfortable, I would never approach women I’m interested in, avoid going out, and just keep to myself. But I know that humans are deeply social and relational creatures, and that being in a relationship would be good for me, since it would help me grow in many ways. Also, staying in too much and not talking to anyone makes me go crazy. So, that’s why I ask if celibacy is a good motivational tool. 

On the other hand, I am wondering if doing this would just make things more difficult. I fear that I could become rather, ahem, outcome dependent and reek of desperation. I also don’t want to be that guy who gets whiplash from every girl walking by and sees every interaction as a possible road to sex.

Anyways, thank you for reading my questions, and keep up the good work!

Stepping Up To The Plate

DEAR STEPPING UP TO THE PLATE: Alright, SUTP, let’s roll this from the top.

First: as a general rule, cold approaches are very inefficient as a way of meeting people. You are functionally trying to convince someone to be interested in starting a potentially romantic or sexual relationship with a complete stranger, often in the span of twenty minutes to an hour. That’s not really how most people meet their partners. While exceptions obviously exist, most folks tend to meet their partners either through shared activities, mutual friends or dating apps; very rarely do you find a “yeah, we were total strangers who bumped into each other at the airport bar” or whatnot.

Working on cold approaches can be good, especially since you can’t exactly count on having a social network in place when you’ve moved somewhere or when you’re traveling, and the skills have a lot of crossover in other areas of your social life. But as an overall strategy for meeting people, your ratio of effort to return is very, very unbalanced towards to the “effort” end of things.

That’s not made any easier by trying to do this in a noisy, chaotic environment like a casino. While yes, Vegas has long played up its “what happens in Vegas” marketing and implying that hook-ups and wild parties could happen at any moment… frankly a lot of that is just marketing hype and a whole lot of folks who are more into the fantasy of Vegas than the reality.

It also isn’t helped when it’s an environment you, specifically, don’t care for and people who likely aren’t as likely to be compatible with. Yes, there are likely to be beautiful women there… but they’re more likely to be into the very atmosphere and environment that you find noisy and chaotic. So you’re going to also be dealing with fundamental incompatibilities. If you want to work on being able to deal with the environment and just get comfortable with approaching and talking to complete strangers, that’s fine… but I think the skills you’re trying to develop would be better served in practicing them in something closer to a situation where you’d meet people you actually want to date.

Think of it as the difference between practicing swinging a baseball bat because you want to get better at kendo or HEMA; yes, technically the mechanical movements are similar, but you’re training for the wrong things.

As for your second question: much of this is going to be based around vibes, chemistry and your connection with the person you’re dating. Sex “should” begin when everyone’s ready, willing and able. Sometimes those things don’t line up at the same time; sometimes they slot into place immediately. One person you meet may like to take their time to feel comfortable and secure before they have sex with someone. Another might be ready to bone down on the first date. It’s going to depend on each individual person and each relationship.

Unless things have been otherwise stated (for example: you or they are somewhere on the asexuality spectrum), it’s safe to assume that the women you’d be interested in dating will know that you’re interested in sex in general. Most dates tend to work with an understanding that sexual attraction is involved to some degree and that a sexual connection is an expected component – if not now, at some point in the future. But just as every woman is different, every relationship is going to be different, and you are going to conduct yourself accordingly.

In terms of bringing it up… well, again, that’s going to vary. If there’s physical chemistry – you and they like kissing or making out, asking if they want to take this to the bedroom is entirely reasonable. If there’s no physical affection or sense of sexual attraction, that might be something to actually ask about. Same with asking a partner you have been intimate with if things have been off; it’s not unreasonable to say “hey, is everything ok? It’s been a while since we’ve had sex and I want to check in with you if anything’s going on…”

But as a general rule, if you’re unsure, use your words. It’s better to ask and risk things being momentarily awkward than to make an unwanted move and guarantee that things will be very awkward. It’s hard to go wrong with “I really want to kiss you right now”, especially during an emotionally exciting point during the date.

Now it’s important to note: you’re entirely allowed to prioritize sex in what you’re looking for when you’re dating. There’s nothing wrong with “just wanting sex”, or making sex a priority in your relationship. People are sexual beings; we have sex for many reasons, including “sometimes we just want to f--k”. It’s far more important to be dating someone who wants the same things as you – or similar enough things, anyway – than to try to subsume your actual desires because you think it’s “inappropriate” or bad. It’s actually worse to try to shove that down and de-prioritize it (again, assuming it’s a high priority for you) in the name of wanting to seem “better” somehow. It’s far worse to find out the person you’ve been seeing has been dating you just to get you in bed and has no other interest than it is for them to say “we want different things, so I don’t think we’re a good fit. Best of luck to you.”

Similarly, you’re allowed to end relationships if the sex isn’t working or if they’re on an entirely different schedule than you in terms of intimacy. Some people will think it’s s--tty, but honestly, it’s far better to end it sooner than later. This way neither of you wastes the other’s time – time that could be used to find someone who is more compatible with you.

If someone wants to wait past a point that you’re willing to, or for conditions that you don’t want or agree to, then you’re well within your rights to end the relationship and move on. It’s far better to find someone who’s on the same page as you in terms of priorities than to either wait it out longer than you’d prefer or try to change their mind.  

As for your last question: look, I’m of the opinion of “it ain’t dumb if it works.” But whether it works… that’s another question. The idea that porn somehow hijacks the brain is both unscientific and ahistorical; it both misunderstands how the brain works and pretends that until we invented motion pictures, sex was an entirely private activity conducted behind closed doors. In reality, for much of human history, sex wasn’t nearly as private or hidden away; even once we started settling in place instead of being nomadic hunter/gatherers, there was very little in the way of privacy when everyone lived in one room huts and homes.

Similarly, as soon as humanity reached the stage of abstract reasoning and representation, we started scrawling dicks and boobs and making representations of naked people and people f--king. Those Renaissance paintings of the various gods and goddesses, nymphs and satyrs? The various famous nude portraits and paintings of odalisques, reclining nudes weren’t seen as “acceptable, classy artistic nudes”, they were porn – paintings to be hidden away in someone’s private rooms, not prominently on display. Hell, Manet’s Le Déjeuner Sur l’Herbe was a scandal when it was debuted and was rejected from the famous Paris Salon.

The point I’m making here is that if you find it helpful to refrain from masturbating or watching porn before you go out to meet people, then great. Other folks find that they don’t feel as pressured or desperate if they rub one out before they go out and about and are able to be a little more clear-headed.

By all means, refrain if you feel like it gives you a bit of an edge or some motivation. But keep in mind that the desire to do things “the easy way” and never take risks isn’t about how much you have or haven’t cranked it. But porn or masturbation isn’t so detrimental as that it would make everyone hermit up if it was strictly controlled, no matter what the no-fap folks say. Having to wrestle with the desire to do things the easy way, to stay in and not take the risks of rejection has more to do with your own psychology, unfamiliarity and a discomfort with being uncomfortable than anything inherent to porn “hijacking” parts of your brain for no reward.

Good luck.

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