How Do I Change My Luck on the Dating Scene?

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Dear Dr NerdLove,

I’m a 33-year-old bi woman. I’ve been single since I was 20 and I’d really like to change that, but I don’t seem to have much luck when it comes to dating.

I’m not on dating apps at all: I recently realised I was demisexual as well as bi and the apps were making me miserable, so I stopped using them as they never really worked for me anyway. Over the past two years or so I started living alone and made much more effort to expand my social circle – mostly so that I wouldn’t go nuts but I also thought that I’d try and make some new friends and see if anything came of that on the dating front as well. I’ve made a really good group of new friends, but they’re all in relationships, and it seems like all their friends are partnered up as well.

I’ve signed up to a few regular activities (a social bouldering event and a book club, as well as joining a couple of D&D groups) and I’ve met some great people, but so far no-one has been interested in dating me. I think I’m reasonably fit/attractive and I dress pretty well – I’m happy with the way that I look, which I think is the most important thing – but I just don’t get approached. I’ve been told I come across as warm, direct and emotionally open, but I’ve also been told I can be quite intimidating.

My relationship history hasn’t been great. My most serious relationship was when I was a teenager – that went on for three or four years but he was controlling/emotionally abusive, and because I was so young I didn’t realise what he was doing wasn’t okay until a while afterwards. Therapy wasn’t as helpful as I was hoping it would be on that front, but time was. About four years ago I had a one-night stand with a friend of five years which I thought would turn into something more but actually ended the friendship. Since then, what tends to happen when I meet someone I like is that I’ll spend ages pining in a way that’s honestly a little embarrassing, then I’ll see if they want to hang out so I can judge the vibe, and I’ll find out that they’re already taken or I’ll get shot down.

It’s not like I think that I’ll never be in a relationship ever again, but I am left wondering why a lot of the things I’ve tried so far haven’t been working. My general strategy is to sign up for stuff and then just be myself as hard as I can and see if anyone is into it. I meet people who I get on with well and share interests with, but 90% of the time they already have a partner or aren’t interested in me. Most of the time I’m reasonably happy with my life but I’m spending a lot of time on my own, especially now that I live alone, and I’d like to change that. I’d also like to explore the romantic/sexual side of myself now that I’m an adult with a more mature understanding of boundaries and standards and while I’m ready to do that, it doesn’t seem like there’s many people out there who are ready to do that with me.

I guess my question for you is – what next? I’ve taken some time to think about what I want and what kind of approaches would be best for me, but so far a change in approach hasn’t yielded anything different. Should I switch things up again, or do I keep on doing what I’m doing? Is there something I’m missing here?

Thanks in advance,

What’s Next

I’ll be honest, WN, one reason why I pulled your question is because you are a direct refutation of the chorus of “women have so many options/never have any problems finding someone to date” that I get from a lot of men. I think it’s important for folks to recognize the difference between what they assume must be true – often based on little more than just “well, it makes sense to me!” – and the reality on the ground. A little recognition that everyone have similar struggles, and developing a little empathy all go a long way towards actually connecting with people as people, instead of a figure that only exists in their heads.

And frankly, a lot of my advice to you is going to be similar to what I tell men who have similar struggles… with a couple of caveats.

Now the first thing I will say is that, when you’re stalling out on dating and having a hard time finding people to date, it’s understandable that you might feel like you need to take some big swings in order to make a change. After all, what you’re doing right now isn’t working; doesn’t it make sense to change up as much as possible?

The problem is: that doesn’t always work the way one hope. Large changes feel like they should produce dramatic results, but often all that’s happened is… nothing. You end up with the same outcome; the only thing that’s changed are the details. This is partially because you are now trying a new dynamic that you’re unused to and many not be authentic to who you are, and partially because that big swing never actually addressed the underlying problem.

And, frankly, any improvements you do make are often temporary at best. The problem with making such wild and large swings is that it takes a lot of your bandwidth and willpower to make it and then to maintain it. It’s a little like someone deciding they want to make major changes to their lifestyle in order to be ‘beach body ready’; they not only make drastic changes to their diet but try to take on an aggressive exercise regimen, restructuring their day to maximize results, etc. It’s a level of change that’s so large and so different that its often unsustainable; one minor setback often ends up being enough to cause them to fall right back to old habits.

This is why my overall advice with trying to troubleshoot one’s dating woes is to make smaller and more targeted adjustments; these are easier to implement, easier to maintain and also encourage you to focus your energy on finding the actual sticking points rather than hiding them under a layer of “new month, new me”.

In your case, WN, there are a couple things that stand out to me. One thing that you mention is that people tell you that you can be quite intimidating. Have the people who told you this said how you’re coming off as intimidating? “Intimidating” is a label with a lot of baggage and subtext when it’s applied to women and AFAB people. Sometimes it can mean a genuinely strong or forceful personality or a tendency to look angry, upset or overly serious when you’re not – much as it does for men. Other times, however, “intimidating” can often mean “doesn’t present/behave according to ‘traditional’ gender roles and expectations”. Someone who, for example, doesn’t let folks talk over them or who’s simply confident or assertive in a way that could be seen as “masculine” or male-coded is often called “intimidating”, when men who behave the same way are unremarkable. Or it may be applied to a woman who doesn’t smile as often or display as much upbeat energy as might be expected from “traditional” gendered expectations.

Understanding what’s making other people think you’re intimidating is important, because it brings up the question of whether this is something that actually needs to be fixed. Many times, it doesn’t – certainly not if the issue is about other people’s (possibly unconscious, possibly not) sexist expectations.

It’s one thing if your behavior is legitimately closed off or unwelcoming – the same sort of “don’t talk to me” body language and attitude you might see from an upset or uninterested man. That’s something you might consider paying attention to, so that you aren’t sending “do not disturb” or “I don’t like you” signals when you don’t intend to. However, it’s quite a different thing to make yourself smaller for the comfort of other people’s egos – people who, quite frankly, aren’t likely to be compatible with you in the first place. In my opinion, it’s better to give the wave-off to people who aren’t right for you than to try to sand down the things that make you unique and special just for the consumption of people who don’t appreciate your authentic self.

A thing I noticed that might – and I stress, might – factor in is when you say “I just be myself as hard as I can”. In general, this is a good thing, and I fully understand that the phrasing is as likely to be hyperbole as a statement of fact. However, is it possible that you’re showing an almost heightened version of yourself – playing to the back row, as it were? If that’s the case, it could be that this is received as being “a lot” or even a little inauthentic, and putting people off. It may help to pay attention to how you’re being yourself; if you feel like you’re almost putting on an exaggeration of who you are, it may be better to dial things back to who you are when you’re putting in your normal amount of effort, with people you’re already comfortable with.

In fact, assuming that people like you already and are comfortable with who you are is a subtle but invaluable way to shift your overall energy when meeting people. By assuming that you’re already friends, you change your behavior and body language to be the same level of warmth, openness and friendliness you give to your friends and loved ones; this encourages other people to respond the same way. It also has the benefit of changing how you are seeing and interpreting other people’s behavior. By changing your expectations, you are priming yourself to see their actions in the most positive and welcoming light, rather than one of wariness, criticism or disinterest.

The second thing is that you seem to fall into a very common trap: you hold back when you should be making a move. This is an area that can be hard to wrestle with if you’ve been taught, as women still frequently are, to put more effort into being approached than to being the one making approaches. You’ve mentioned that people aren’t approaching you, so perhaps it’s time to stop waiting and to start taking steps yourself.

Part of this means that you’re going to have to learn to recognize, and then break, some of the patterns you’ve been repeating. You mention that your usual pattern is to pine for someone for ages, then try to hang out with them. It’s understandable behavior; you want to wait to “be sure” or gauge whether they might like you. There’s also something a little romantic about pining away for another person. But the problem with this is that you end up wasting time while also increasing the likelihood that the other person will either be uninterested or unavailable. Not only does this mean that you’re investing emotionally in someone before you’ve so much as really talked to them, but you’re not making any sort of actual forward progress and they are.

You might be waiting for the stars to align and for the signs to be right, but they aren’t waiting with you. They can’t take you on a date if they don’t know you’re interested, and the longer you wait, the greater the odds that not only do they think that you aren’t interested, but that someone who is interested is going to make their move.

If you can recognize in the moment when you’re sitting on feelings of attraction for someone, then that’s your sign that you should stop waiting and, at the very least, go talk to them. The waiting doesn’t do you any good; it neither increases the odds of success nor minimizes the sting of disappointment. Asking sooner may not make things “safer”, but at the very least, it means you don’t waste time and energy on them. Getting an answer, even if it’s a “I’m flattered but no thank you”, means you’re free to move on to find someone who is interested.

But there’s a gendered component to this too, especially if you’re interested in exploring your attraction to women. One of the cliches among women who date women is “lesbian sheep syndrome”, where everyone is waiting for someone else to make the first move and – as a result – nobody does, and everyone goes home frustrated.

Well, since someone’s gotta make the first move, it may as well be you. Waiting for someone else to approach you hasn’t been paying off, so there isn’t exactly a downside to choosing to be the initiator. After all, approaching people you like, instead of pining away at a distance, isn’t going to make them double ignore you.

Think of it as hanging out your shingle that tells people you’re (metaphorically) open for business. People aren’t mind-readers, after all, and they’re going to interpret someone standing out on the sidelines as not being interested. Making the first move, at the very least, will let people know that you’re actively interested and looking, instead of having to guess based on context clues.

The last thing I would suggest is that you may want to start asking friends to spend time and hang out, and to create opportunities for group hang-outs among the new friends you’ve been making. You’ve mentioned that you spend a lot of your time alone. This, too, is something you can correct with deliberate action. It may help to invite people to join you for things you’re already planning on doing, rather than hoping to make plans with someone. Asking someone if they want to come along is both mentally easier for the person doing the asking, but also for the person being asked. For the former, you’re not building your hopes around their saying yes or making doing the thing conditional on another person’s participation. For the latter, it’s easier to say “yes” to an already existing plan than to feel like someone’s making plans specifically for you – especially if you two aren’t that close as friends yet.

Getting in the habit of inviting more people to spend time with you will help shore up some of the friendships you’ve been making, but it will also get you in the habit of being the one to actually make moves and initiate things. When you have built up the emotional muscle memory via lower-stakes asks, it’ll be that much easier to make a move when it “counts”.

Good luck.

***

Dear Dr. NerdLove:

My wife and I have been together for fourteen years, and lately, we’ve been working hard to rekindle the passion in our relationship. Like many couples, we’ve had our ups and downs, and for the last couple of years we noticed that our sex life had lost its fire until it nearly went out entirely. Our libidos weren’t in sync, neither of us had been feeling particularly motivated to initiate sex with the other, and we eventually realized that we had gone for months without actually having sex. After attending couples counseling, we realized that the main issue was boredom; the sex we’d been having had been routine, passionless and ultimately unexciting. Our sex drives had dwindled because when we did have sex, it had been pleasant but frankly dull.

Since then, we’ve both been committed to trying new things in the bedroom, which has brought us closer, helped improve our communication and it’s brought our sex life roaring back. It’s been exciting to explore different fantasies and ideas together and actually putting them into practice. We’ve had a number of wild adventures recently that’ve been whetting our appetite for taking things to a new level.

Recently, we’ve started talking about trying a threesome, which is something we’re both intrigued by, but only recently felt comfortable revealing. My wife in particular has been interested, both in being with a woman, but with seeing me with another person as well. We feel it could be a way to bring some novelty and spice into our lives, but we’re also a little nervous about the logistics.

Neither of us has any experience with this, and we’re not sure how to go about finding the right person or how to ensure that everything goes smoothly. We’ve heard the various horror stories of jealousy or unexpected emotional reactions, of boundary-pushing and of course we’re painfully aware of the cliches of the suburban couple propositioning friends. We don’t want to introduce drama or hurt feelings into our marriage, and we want to make sure that we’re both comfortable with the experience. Plus, there’s the practical matter of finding someone who fits with our relationship dynamic.

We’ve heard mixed advice from friends, and we’re wondering if you could offer some guidance on how to approach this. What’s the best way to find a third who’s respectful of boundaries and aware of the complexities of a married couple exploring this together? How can we ensure that everyone feels safe, respected, and clear about expectations? And most importantly, how do we handle the emotional aspects, so we don’t end up feeling jealous or insecure afterward?

Seeking A Guest Star

I always find it a little amusing when people who realize how their sex life wasn’t meeting either of your needs seem to leap to threesomes to a point that it feels like there’s a script.

Don’t get me wrong, the old cliché of “life after death is as unlikely as sex after marriage” is a cliché because how infinitely adaptable humans are. No matter how exciting something can be when it’s new, it can easily become routine over time, and once it becomes routine, it can become dull or even tedious. And while I’m always in favor of sexual adventure and experimentation with your partner to keep things hot… the prevalence of threesomes as the chosen option makes me wonder if it’s become a meme, a way of folks dipping their toe into polyamory or something similar, or if it’s just the way people position it like the Everest of sex.

I feel like some enterprising doctoral candidate could get a paper out of this.

But that’s not the point; you and your wife are taking those positive steps to bring back the spark and find new adventures with one another, which is excellent and should be applauded. Planning a threesome can be tricky; there’re a lot of ways they can backfire on you, so let’s make sure you stick the landing.

Now as for your prospective threesome: there’s the logistical angle and then there’s the emotional one. Threesomes can be tricky, in part because they can involve navigating a number of emotional landmines. Part of the problem is that you may not even know those landmines are even there until someone hits one. Seeing your partner (or their seeing you) kissing someone else might not necessarily trip anything for you… but seeing them face down in another person’s lap (or riding them or…) very well might.

There’s also the fact that threesomes can’t be equally about all three people at the same time. There’s no practical way for everyone involved to be receiving equal levels of attention at all times. Someone’s going to be the focus of more of the attention, and there’re frequently times when a threesome becomes more of a two-some, with one person sitting on the sidelines. That can leave the person on the outside feeling neglected, excluded or jealous – feelings you definitely don’t want to have during this fun little escapade.

So the first thing you and your wife need to do – before you’ve even started looking for your prospective third – is to hammer out what you expect, how you want this to proceed in an ideal world and to lay the groundwork for how you’re going to deal with any emotional issues in the moment. You might, for example, want to agree that for the first time, making out and oral sex with the third party will be fine, but penetration is reserved for the two of you if it’s even on the table at all. You want to talk about how you would handle emotional issues that could come up without warning – including possibly having a safeword that would serve as pulling the emergency brake if need be.

You should also talk about where attention and focus is going to be directed. Are you seeing this, for example, as the two of you lavishing attention on the third person? Or is the goal fulfilling your wife’s fantasy of seeing you with another person? Talking about what want this experience to be about will help shape expectations, as well as how it’s going to proceed in the moment. The event tends to proceed a lot more smoothly if, for example, you know the point is for one person to get the lion’s share of the attention instead of playing it by ear and hoping you figure it out in the middle of things. That is a good way up the odds of hitting a landmine or two.

These issues are also something you should be discussing with your prospective third – ideally days before you all get together to play. Setting expectations and ground rules well in advance – and not changing them in the middle – is going to make your first threesome a much more enjoyable experience for everyone. I realize that this feels like a lot of talking and planning for sexy fun times, but this is a case where planning prevents disaster. Don’t expect the the spontaneous threesome where everything just flows perfectly; that’s the fantasy version from porn. In the real world, a spontaneous “we saw you from across the bar…” threeway is often as fumbling, stop-and-start and occasionally awkward as the first time with a new person. Knowing what’s expected and how it’s going to proceed will make everything flow much more smoothly and enjoyably.

But of course, this also necessitates finding your third. And this is a place where, frankly, I think you would be better off with hiring a professional. Find an independent escort who works with couples, fill out their screening form, pay a deposit and start planning the date.

While there’re a number of options for finding a prospective third, from an adventurous ex you’re still on good terms with, to creating a couple’s account on a focused app like Feeld, hiring a sex worker not only ensures you find what you’re looking for, but will ultimately help you avoid a lot of potential drama bombs. Yes, it does take away a little of that “Cinemax After Dark” sexiness of trawling a bar or bringing it up together to someone you both know, but again: the fantasy ignores all the potential pitfalls that reality is heir to. Among other things, a professional escort is going to be more receptive to “here’s how we see this happening”; their job, after all, is providing the service you’re looking for. Engaging their services also has a much lower risk of triggering drama or feelings of jealousy. The two of you are far less likely to worry that they’re going to be some sort of threat to your relationship or being more into one of you than the other, the way you might with a friend or a stranger. And, just as importantly: you also aren’t going to have the question of “so… what now?” afterwards. There aren’t questions of “does the third stay over?” “Who stays in which bed or which bedroom?” or any related logistical issues. An escort’s there to do the job and to leave, quietly and discretely when the time’s up.

The key, of course, regardless of who you invite to join you, is to treat them with courtesy and respect – whether they’re a professional, a friend or a person you’ve met via the apps. The worst thing you can do is treat this person you’ve invited on this adventure with you as a toy or a tool. It’s dehumanizing, it’s callous and it’s a horrible thing to do to another person who’s made it possible to fulfill this fantasy. If you want this threesome to be a success and possibly the first of more to come (er… as it were) in the future: treat your guest star like a guest, not a sex doll. Even if you don’t see them again, it sets the tone for future engagements… which may include someone you’d like to see again. And again.

Good luck.

—

This post was previously published on doctornerdlove.com.

 

The post How Do I Change My Luck on the Dating Scene? appeared first on The Good Men Project.

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