DEAR DR. NERDLOVE: I have been married for 15 years, and together with my wife for 18, with two children (13 and 10). Two years ago, my wife explained that the marriage was over. We stayed together, largely for financial reasons, until I was able to move out some five months ago.

After so much time in a monogamous relationship, I am now in a panic about dating.

I have tried online dating – your favourite, OkCupid – but have had two replies to 10 messages so far. The two replies have both been from the most speculative messages, courteously explaining that they are not interested. Nobody else has even acknowledged my contact, even though I’ve carefully shown that I have read their profile, chosen people with whom I have, apparently, plenty in common, and couched my message in civilised and articulate terms. (For the avoidance of doubt, I am not messaging young women, but ones of my own, mid-50s, age group or up to 10 years my junior.)

I appreciate that people often do not reply to messages, but a complete absence of interest is disturbing. I am an attorney, self-employed, with a wide range of interests. I have no problem talking with women – in fact I find female company a lot more congenial than male company, and I have plenty of female friends – and although I will never have a career as a male model, I’m in pretty good shape for my age. I suspect the problem may be the fact that I am separated, rather than divorced, but there is nothing I can do about this – under English law, you can’t get a divorce within two years of separation unless you are going to allege adultery (we have both been faithful to each other) or “unreasonable behaviour”, which opens a whole can of worms of unpleasantness. I’m getting the sinking feeling that I’m facing at least two years more of celibacy. (In fact, there are a couple of real drawbacks to me as a romantic prospect – thanks to the recession my legal practice does not produce much money, although things have improved over the last couple of years, and because of the children I still see a lot of my wife and we still cooperate to a great extent in practical matters – believe it or not, we still have a joint bank account and I run the finances for both of us. If a woman found either of these points unattractive, I would not be surprised – however my complete failure so far is in advance of either of these points coming up.)

So morale is pretty low as far as online dating is concerned. Meanwhile, the more traditional approach of meeting people through my range of outside interests (I play in an orchestra, play volleyball in a mixed league once a week, am in a mixed book reading group, and have joined a couple of meetup groups) or getting together with one of my female friends looks very problematic. (And, of course, a major disadvantage of working for yourself is that I have no co-workers at all!)

Before I was married I always had a problem with converting contact with women in a neutral social setting into a sexual relationship. If I joined an evening class, for example, my thought process was always that if I hit on one of my fellow students and was rejected, I would become in some way a pariah in the class – and I always made the mistake of joining classes where I actually wanted to do the study programme – or if I was in a club I would avoid any entanglement with other club members, lest it ruin my participation in the club activities – I would never dare make a move on one of my fellow volleyball players, for example.

Pretty destructive thinking – and it’s been made worse by something that happened in the last month. My wife and I have a mutual friend with whom I have been on very friendly terms for a number of years. Since the separation we had taken to having coffee together once a week for a prolonged chat, and we see each other around the village a lot anyway. It has been the kind of relationship where if we are both at the same party, we will form a huddle in a corner and talk for ages. Unfortunately – you can see where this is going – I like her a lot, and made the mistake of asking her whether I should rule out in my mind the prospect of our friendship developing any further. She expressed herself interested, but saw practical problems; the next day I texted her that I appreciated the problems and that it would not affect our friendship if she said no, and she replied that having thought things through any relationship would have to be surreptitious and that would not be good for either of us. Then she blanked me. The coffee mornings have stopped, the last time I saw her in the village she walked past me without saying hello, and as far as I can see more than 10 years of friendship have just gone up in smoke. 

So, about as tentative an approach as possible to somebody with whom I have for years been very close, with the express statement that I would not hold it against her if she could not respond, and it’s a fiasco. I think you can guess what the prospects are now for me risking making any advances to somebody that I know through a social setting where I want to remain in that setting – I may meet somebody socially, but am frankly terrified that unless I remain 100% platonic, I will need to get out of that social setting for good. (Concrete example, I found there is a local hiking group for singles – decided against joining it, simply because of the thought that I would have to leave the group as soon as I had attempted to make my move.)

Any advice? Is it just a matter of getting a grip on myself? Or do I accept I’m on the shelf for the foreseeable?

– Unfrozen Caveman Lawyer

DEAR UNFROZEN CAVEMAN LAWYER: First of all: welcome to online dating. I recently released a video on the Dr. NerdLove YouTube Channel (youtube.com/user/DrNerdLove) where I talked about how to deal with the frustrations of dating. One of the biggest issues is that men and women use dating apps like Tinder and OKCupid very differently — men try to pick everyone and then narrow things down after they’ve matched. Meanwhile women tend to be more selective in the men they match with and swipe right on far fewer matches than men do. As a result: women are matching with men who may then decide never to message them, while men are encouraged to swipe right as widely as possible in order to maximize the chance of getting ANY messages… even with people they’re not actually attracted to.

Small wonder online dating is so messed up right now.

But even when you do match with someone, sometimes it just won’t work out the way you would hope. Lots of people will just not respond to emails for a multitude of reasons ranging from accounts not being active to seeing how things are going with other matches to having arbitrary deal-breakers that you just somehow hit. Again: this is just how online dating goes, for both men and women. There will be a lot of shouting into the void – and conversations (and dates) that ultimately go nowhere. As the saying goes, every relationship fails until one doesn’t… every approach in online dating fails until, once again, one doesn’t.

On paper you sound like a pretty darn good catch. If this isn’t coming across in your profile, then you may need to consider revising it. You should definitely have a friend look over your profile, especially a female friend you can trust to be bluntly — if insightfully — honest with you.

However, I suspect the problem goes beyond the vagaries of online dating and far more about where you are mentally and emotionally. To put it mildly, you sound exhausted and depressed as hell. You have an incredibly pessimistic attitude towards yourself and dating and if it’s coming across to me, then it’s definitely coming across to the women you’re interested in. And to be perfectly frank, I’m not bloody surprised.

Dude, your relationship of nearly 20 years came to an end and you couldn’t even make a clean break of it – you continued to live with your wife, knowing that the relationship was over and only got out for good five months ago. For f*ck’s sake, that is not enough time for you to heal and recover. You don’t have emotional scars, you have emotional hemorrhages. You’re still one of the walking wounded. You shouldn’t be thinking about dating right now, you should be working on healing yourself. What happened to you was a massive emotional blow and even though you don’t realize it, you’re still reeling from it. I don’t necessarily believe in the old saw that it takes roughly half the time you were together to get over someone, but five months is not enough time to leap back into the dating scene, even on a casual basis.

You need to quit worrying about dating for now; you’re just not ready for it. What you need to do is focus on yourself for a while. Your goal should be getting your life back in order and your head on straight, not trying to find a replacement spouse. I realize right now you’re feeling like you’re never going to find someone who will love you ever again and you’re desperate to prove yourself wrong but all you’re doing is making things worse. You’re not seeing things clearly. Look at what happened with your friend. You thought you were confessing your feelings to her; she on the other hand was hearing you completely recontextualize your relationship . To her, your asking if you had a chance with her sounded like you were admitting that you’d had feelings for her this entire time… including while you were with your wife, who she’s still friends with. So now not only are you hinting – inadvertently – that you’ve been in love with her for the years while you were married, but that you’re asking her to potentially betray her friend’s trust.

(Yes, you can’t call dibs on people, but think of how this looks from her end of things.)

No wonder she’s pulled the fade.

If your pain wasn’t still so fresh and raw, you’d realize how it looked too.

So take dating off the table. It’s just not in the cards for you right now and not putting pressure on yourself to be back on the market it is going to actually make you feel better. You are not open to finding a new relationship and probably should be for at least the next year or so. Focus on your job, your finances and your relationship with your kids. Rebuild your life and get deeper involved in your interests and hobbies. Join groups just because it’s something you want to do, not because you’re trying to find a new girlfriend. Make new friends just for the joy of having friends. Let the pain fade and the wounds heal, let yourself face mornings without dread or self-recrimination.

I’d also suggest talking to a therapist. You’re seriously depressed right now and I think being able to talk about your anxieties with someone will do you a world of good.

And when you do recover to the point of being able to date again – remember, at least a year, if not two – just asking somebody on a date doesn’t mean you’re going to be exiled from your social group. As long as you’re polite about it, take rejection with aplomb and grace and don’t treat it either like a dire insult or the end of the world, nobody is going to get weird. If she says “thanks but no”, then your response is to shrug and say “ok cool. Hey, did you hear about Arsenal’s striker….” and just let it go.  If you don’t treat it like a big deal, nobody else will either.

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 wanted to start off by saying that I love your site and articles, keep up the great work.

My question is part personal finance and dating. I’ve been single for the past 2 years now and it’s been great. I’ve been able to travel, pursue my hobbies, and simply have fun on my own terms. However, now I’m approaching 30 years old and starting to think about dating and finding someone special in my life. The thing is over the past 4 years I racked up a considerable amount of consumer debt. A few embarrassing financial mishaps happened and I decided to set myself straight. I spent the past 6 months learning everything I could about personal finance and getting them in order. I have a stable government job that I enjoy. I adhere to a strict budget, adjusted my lifestyle, got rid of my car, moved back into my parents, and reduced a lot of frivolous expenses. If I can maintain my stick to my new financial plan I expect to be debt free in February. I’ve done several “bootcamps” and a lot of reading and listening to material such as your blog, so I have a good understanding of how to meet girls. My question is should I spend more money on going out partying, and trying more activities to meet someone by pushing back my debt free day? 

From my male biased perspective it seems that not having a car and living at home with my parents is not very attractive, even though I know a lot of my peers live at home due to the current economic state. So should I wait until I am debt free move out and then start dating? I’m also thinking that if I do that I am giving up almost two years of searching time and that I may miss “the one” during that period. Right now my entertainment budget is minimal and I am almost sure I would go over if I started dating again. Dating requires money going out for dinner, parking, drinking, concert tickets, out door activities, lunches all that great stuff costs something and it can add up quickly especially if I’m seeing more than one girl at a time. I don’t want you to get the impression that I buy everything for girls and want to be their sugar daddy. I am cognizant of not falling into that trap and not to attract those type of girls. I imagine there are only a limited amount of cheap things to do like picnics, free galleries, and bike rides. What are your thoughts?

– Credit Card Slave

DEAR CREDIT CARD SLAVE: First of all, congratulations on getting your life in order! Financial debt is out of control in this country and absolutely ruining people’s lives. Getting everything paid off and keeping your head above water is no small accomplishment, especially with the economy the way that it is right now.

Now as to your question.

Dating, like life, does take a certain level of spending – food ain’t free, after all –  but if it means going into debt to do so… well, you’re doing it wrong.

Part of what you need to do is think about the types of women you’re interested in. If you’re looking for a woman who wants to go out on the town every weekend, likes to go dancing at clubs, wants see the latest movies in the theater and eats out on the regular… well, you’re probably going to be better off giving yourself time to build your finances up more. If you’re looking for someone who can appreciate creative dates, Netflix, picnics, museums, hikes and home-cooked romantic meals, then you’re in luck.

Dating can be done – and done well – on the cheap, even if you’re seeing more than one person; it just takes careful thought, creativity and planning. There are more cheap and free date activities out there than you’d think; you have to be willing to do your research in advance. To start with, start scanning the local alt-weekly or local subreddit; these will have all sorts of listings for cool events that are free to attend, from speaking engagements, gallery openings, local theater performances, classes, Farmer’s Markets, craft faires and film festivals. You should also find Facebook groups that talk about current events in your area and check NextDoor and other local sites for various goings-on. The more you know about what’s happening in your city, the more cheap date opportunities you’ll find.

Also: just because something is cheap doesn’t mean it’s a lousy date. Museums, for example, make excellent dates. They’re classy, they offer plenty of topics for conversation and most of them ask for voluntary donations rather than a set price. Picnics, hikes and bike trips can all be insanely romantic with just the two of you taking in the beauty of nature. You may not be able to go out to dinner on dates but that doesn’t necessarily mean that you can’t date at all; I’m a huge fan of the “romantic homemade pizza” date – you collaborate on ingredients and make a pizza from scratch at your place or hers and then enjoy it with candle light and a nice bottle of wine. Pizza is awesome because the ingredients are cheap, it’s easy to make and it looks really impressive… and everyone loves pizza. 

The great thing about dating on the cheap is that by having restrictions, it forces you to get creative and that is going to make you more appealing to women. Sure, anyone can do the traditional “dinner and a movie”… but how many women have gone tubing down a river for their first date? Or went to a kite festival or a flower show at the botanical gardens? These are going to make you stand out in a good way amongst all the other guys out there.

The biggest problem you’re honestly going to have is logistics. Living at home and dealing with public transport can be a problem – not because it’s bad but because it’s going to be considerably less convenient than if you have your own place and your own car. Everybody’s been f

ked over by the economy; nobody’s going to blink twice about the fact that you’re taking the bus or the subway or that you’re living with your folks to get out from under your debts and save up your cash because everybody’s had to tighten their belts. If the women you’re dealing with are  going to look down on you for getting your finances under control… well, frankly, you’re better off not dating them in the first place.

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: How can I look less intimidating and scary and more open and friendly? Or more interested in dating in general? 

Thing is, I am 21 years old virgin who have never been in romantic relationship before. I suppose I am late bloomer – I haven’t been interested in guys, dating and sex until very recently. There also have never been many guys around (my majors both in the University and high school were to do with liberal arts which meant that most of my class-mates were girls) so I am kind of not used to communication with them and to be honest a little bit afraid of them. 

But apparently they are afraid of me even more. Or so I’ve been told many times. It appears that by first impression I always look like I am made of ice or iron, very reserved and strict as if I am silently judging everyone and generally hard to approach. Which is not true at all, I am very happy if people approach me at parties and the likes and love to meet new people in general. Still, it seems guys of my age find courage to talk to me only after consuming lots of alcohol. (Older men is another story though, I’ve been told that I usually behave not like my age but much older and that seems to attract men over 40 who usually have wives already). 

How to change that? Smile to everyone around me? Change something in body language? 

Also, many people seem to assume that I already have a boyfriend. Maybe I look so uninterested that people think that I’m already attached? What one should do to show that they are interested in dating? 

I don’t think that I am unattractive, rude, mean or that socially awkward yet I am single. My parents and friends pressure me a little bit to find someone and maybe I do feel a little lonely while watching romcoms and yearn for some affection. That’s why I decided it’s time to do something about the impression I have on people so when I finally make myself go to those magic places where you can meet a lot of single guys I keep hearing about I’ll be ready. 

I would appreciate any advice and would like to thank you in advance! 

PS: I am sorry for bad grammar; English is not my native language. 

Iron Lady

DEAR IRON LADY: Without seeing you in person, it can be hard to diagnose the problem… in as much as there is one, anyway. To start with, it could depend on the people you’re hanging out with. A lot of liberal-arts types are often shy or introverted, possibly even a little intimidated by you; a lot of guys get anxious over the idea of approaching someone they find especially attractive because they fear they may not measure up. If you’re especially driven and ambitious, they might worry they have to be at least your equal or you might not consider them “worth your time”. As a result: it takes a little booze to ease the anxiety and serve as a little social lubricant.  Older men tend to be more secure in themselves, especially with younger women; they’ve frequently worked through their hang-ups and often feel that their age gives them a leg up, status-wise. This may be part of why so many older gentlemen feel comfortable approaching you; they feel like they’ve got less ego on the line.

Keep in mind: this is their problem, not yours. If a guy is intimidated by your accomplishments – perceived and actual – then they need to work on their hang-ups.

I suspect though that at least part of this has to do with the fact that you’re a late bloomer yourself. You haven’t had much social experience and you’re more a little intimidated by guys yourself. This may be causing you to come off as uninterested or reserved when in reality, you’re actually just a little shy. I would start by checking your body language. I’m guessing you tend to stand a little pointed away from other people, possibly with your arms crossed. This tends to read as “closed-off”; holding your arms across your torso  – crossing your arms, holding your drink like a shield, etc. – is often a defensive look that says you’d rather people keep their distance. Pointing your body away indicates that you’re directing your attention elsewhere, which carries the message that you don’t have any interest in what they have to say. Letting your arms hang loosely at your side, letting your body relax so you don’t look like a soldier at attention and angling your body towards the people you’re talking to will come across as much more open and approachable than someone who seems like they’re inspecting the troops.

I also suspect that you may not be smiling much, or at least that your smile isn’t necessarily being “read” as a smile to others. You’ve almost undoubtedly have heard of “Resting Bitch Face” used to describe people who seem angry or stern when they’re not making the effort to smile. It’s obviously a term that was coined for comedic effect but there are people – women and men – who come off as stone-faced or even angry without intending to. In fact, this is a problem I’ve had to work on; I may be having a good time, but people think I’m upset because I look so serious. I’ve had to make a conscious effort to smile more – a wider, more obvious smile than my usual sardonic smirk or solemn mien.

It seems silly, but practicing holding a friendly, inviting smile can help, especially if you’re not terribly expressive on a day to day basis.

Now, one thing you can do in social situations where you’re looking to meet people is to give what some call “approach invitations” – in this case, meeting someone’s eyes and then giving them a smile. Some folks respond well to the classic “meet the eyes, look away, meet the eyes again and smile”. Both of these are natural signs that you want them to come over and talk to you.

But while this is all well and good, I’d also advise you to take your social life in your hands and approach guys you’re interested in rather than waiting for them to notice you. If they’re afraid that you’re cold and unfriendly, coming up to them and saying “Hi, you seem like you’re cool and I wanted to meet you, my name is Iron Lady…” is going to let them know you really are a warm and caring person they should get to know. Don’t be afraid to be willing to make the first move, including asking them out on dates; luck tends to favor people who make their own opportunities rather than waiting for them to happen. It can be a little nerve-wracking at first – ask any guy about how nervous they get about approaching someone they’re attracted to – but experience and practice will help you get more comfortable making the first move and getting to know awesome people.

Good luck!

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