The Savvy Dater: How To Make People Think You Have It Together When You Don’t

Name: Danielmandivorce
Comment: My question is this…

1. I am 32, single and have been divorced for two years now. After my divorce, I had no other option, but to return home and live with my parents. I have tried Craigslist, and pretty much any dating sites that are out there. I only started this recently.

2. So, How do I ask a girl out? Also, how do I approach the subject of me still living with my parents to the girl that I am asking out?

3. I am tired of being single, I want to find my equal… Meaning that I want that glint back in the corner of my eye. I want to be happy again. Please, if I am doing something wrong, then tell me. I would rather know now, then later. Also, if you have any tips for me, I would greatly appreciate it. Thank you!
Age: 32
City: Norfolk
State: VA

I’m not going to lie. Living with your parents is going to make things difficult for you. While it’s understandable that, after a divorce,  things might not be great for you financially, someone who has never married or possibly even lived with anybody might not understand why. So my first suggestion is to focus on dating divorced women. They will have a basic understanding of your situation.

Obviously, living on your own would help your situation significantly. Can you get a roommate? You don’t mention much about your situation other than you’re divorced. Do you have children? Are you working? If you can’t afford to live on your own, how do you expect to be able to afford the costs that come with dating? It makes sense that you’d like to start getting back out there, but you have to be realistic about what you’re up against. Dating can be expensive. Especially if you’re dating online. You’re going to have to compensate for living with your parents by not skimping on dates.  That doesn’t mean you have to go all out, but $20 coffee dates just aren’t going to cut it. I would also move to a paid site. Your situation kind of requires that you demonstrate that you are willing to pay and are not bordering on the poverty level. You don’t want to be on CL or Plenty of Fish. Try OK Cupid and Match. Your photos need to make you look like you have your life together. You need to look happy, neat and polished. There can be no traces of sad sackery in your profile text. The best approach is to maximize your positive attributes and spin your story. Telling women you moved back home after divorce because you had no other options is Sadster 101. A better explanation Is that you moved home to save money. You don’t have to say for what. Showing financial responsibility and that you have a financial plan for the future will work to your benefit. These women you barely know don’t need to know your whole back story.

I’m torn between advising you to be upfront about your situation in your profile and waiting until you are exchanging messages to reveal your living situation. I would definitely reveal it before you meet. Personally, it would annoy me to find out on a date that the guy had roommates or lives with parents. That’s one of the few “probing” questions I ask when exchanging messages with someone. I start off by asking in what part of the city they live and then ask if they live alone. I don’t date men with roommates. We’ve covered this. It’s a lifestyle choice that many people have.  If you’re situation involves you living in a completely separate extension of the house, then that’s more workable.But if you’re living in your old bedroom, you’re going to have trouble. Sorry, but you are.That’s why it’s important to come up with a story that is (mostly) true that highlights your positive traits.

When you do get to a point where you’re ready to ask someone out, the main thing to remember is that confidence and assertiveness is key. Don’t drag your feet and don’t hesitate. What most women want, I think, is a guy with a plan. Figure out where you’d like to take them once you’ve chatted a bit. Find a place that works with your budget. Have your schedule organized so you can suggest a couple of different nights. Don’t be vague or wishy washy. Exchange a few messages and then suggest that you and she meet up. Easy peasy.

Your real priority here should be getting back on your feet. Maybe you should wait to date until you’re in a better financial position? Dating can be brutal on someone’s self-esteem. You already sound somewhat emotionally beaten down. Maybe put dating on the shelf a bit until you feel more settled?

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19 Responses to “The Savvy Dater: How To Make People Think You Have It Together When You Don’t”

  1. noquay Says:

    I really think the OP needs to get his life together first. You cannot take a woman to your home and yep, dating is expensive; meals, gas money, upping your looks. There was a period of time where my dad lived with me and I had no social life even though it was a case of ME supporting HIM. The only time I have heard of an instance where it was OK for a man to move in with his folks was a case where he was severely injured and bedridden for a long time. Unfortunately the OP will be judged as a deadbeat simply because there are so many men in his age range and living situation that ARE. Sad but true. One step at a time. If you must meet women right now, do so IRL so they get to know you. I am afraid you will be written off on line.

    • Howard Says:

      Life is not fair. We have to accept that. While a woman may get away more with such a situation, living with parents after a divorce, a man simply does not get away by our society standards. I could also in turn expound at length about the things men get away with and women can’t. So women face similar issues too regarding fairness.

      When humans have faced seeming contradictory unfairness through time, we have developed many defense mechanisms to combat these situations, to achieve some levels of the things we want in life. These solutions are never perfect. And we are always guaranteed that the people who enjoy the advantage are going to criticize and villainize the dispossessed trying to get at least some modicum of what she or he wishes. Look at the Jim Crow South and people of color. Look at the feminist movement. Look at the LGBT struggles.

      So, Daniel, your options for trying to get some emotional happiness in your life will be greeted by jeers for a lot of holier than thou women who would want similar emotional happiness, if they were in your situation. You may indeed have to lie by omission. We all deserve some emotional happiness in life. Our society has slowly transformed over time to insidiously seeming to say only the successful should get this or that. While this may hold some truth regarding material possessions, it certainly is a crock of shit when it comes to emotional needs.

      Some would say, your perfect solution is someone in the same position as yourself. This could work, but something tells me that a woman in such a position could be looking for a guy who can help her, and not necessarily a guy like you. So you may be back to lying by omission.

      Don’t give up hope though. Yesterday, I saw a homeless couple panhandling at a street corner. There will be women in similar situations as yourself who would date you. There are women in better financial situations who will also date you. Look in places like the church or organizations that have people doing volunteer work. People with raised spiritual consciousness, tend to avoid judging people simply based on things like living with their parents.

      The women on this board are the type of materialistic people you exactly want to avoid.

  2. mari Says:

    I agree with noquay and Moxie – not sure what your financial circumstances are – but basically you have to move out of your parents home in order to date online. You can have the smallest apartment as long as it is yours. Assuming this is impossible, then Moxie is right, need to somehow spin it and see what happens. Sure there are women who live with their parents too who won’t find this surprising, but with both people living with their parents not sure how you will have a romantic evening. Anyway – confidence goes a long way and being upfront about your living situation is important. My current bf is divorced, two kids in college, recently moved back to NYC and rents a room in an older women’s apt. Told me first date – I have my own “red flags” so it all worked out..but was important that he told me.

  3. AnnieNonymous Says:

    There are a few ways to spin the fact that he lives with his parents. I live in an area with a VERY high cost of living, so sometimes I feel like I’m choosing between guys who live at home or guys who live frat-style with five roommates. I don’t know a single guy in my dating age range who lives totally on his own. This guy should ask some female friends how they’d feel about dating a guy in his situation. He should also emphasize other reasons why living with his parents is the right choice for him right now. Is he finishing grad school, with a set graduation date (ie, does he have circumstances that line up with a timeline for getting back on track)?

    Was the divorce particularly bad? Does he have kids? There’s something he’s not owning up to here. If he was paying at least 50% of the rent or mortgage on a house with his wife, why wasn’t he able to live on his own right afterward? Why is he still grappling with this after two years? Is he even working? Was his ex-wife wealthy and covering all of the expenses?

  4. D'Alias Says:

    ^^^ yeah, I’m going to assume you don’t know a lot of divorced people. Def takes more than two years to recoup for lots of people. Many divorces aren’t even settled in that amount of time.

    OP, it’d be great if you could get things together first but if the horizon isn’t in sight then why wait? You CAN date while living at home but then you’ve got to compensate for it differently. For instance, you always drive. Or always pay. Plan frequent weekends away. Be willing to date people in similar situations (roommates or parents) & agree to sublet a room
    together to see how it goes. Even if it’s basically just a sex pad that works if you both really live at home.

    Do NOT put this info in your profile!!!! You’d sound so weird and pathetic for over sharing. But DO disclose early on (via phone or in person). I know plenty of men here in NYC who live at home and manage to date (usually their own floor of a two fam, or slowly took over most of the bills from aging parents, single dads who pay child support equivalent to a rent payment, etc). It CAN work.

    • AnnieNonymous Says:

      People are being flippant about the divorce because of his age, not because of “not knowing divorced people.” Daniel is 32 and got divorced at 30. Realistically, how long can we assume that they were married? Probably not long enough to amass many assets, and he doesn’t mention having kids. The point is that there’s something he’s not admitting about his finances. I’d need more information about why a man in his 30s can’t come up with the $500 it takes to rent a place with one roommate in Virginia. Was the divorce that bad? Does he have a lot of student loan debt? Does he actually have kids? Because having kids and/or not being officially/legally divorced are bigger red flags to women in their mid-20s than living with your parents is.

  5. VJ Says:

    I’m with DA & AN here, this is not an unusual situation, especially for the times and the ages involved. Again what part of the Depression did you not understand the 1st time?

    So lets run down what we know:

    1.) Men’s income has been Flat or Declining for the better part of 30+ years. This is now true for even College educated men too, for many complicated reasons. Blame Outsourcing, robotics, off shoring, declining Unions, the hollowing out of the middle class occupations, and of course bad economic times with forced governmental austerity too.

    2.) Dudes previously Married, despite being ‘pre-qualfied’ For another marriage in most instances, are commonly stretched further still, depending on the divorce decree, child support, moving expenses, new jobs, etc., all possibly required by the Courts or circumstances.

    3.) So Yes, there’s bunches of guys in the same boat, and often they’re in the same very crowded & expensive cities too. Failing to come up with a nice ‘room to let’ (hard to find in this day & age), you’re left with roommates, living with relations/friends, parents, or a really cheap run down place ‘upstate’ or well out of the metro area. That’s it for affordable housing on a tight budget outside of very dangerous slums. That or the long wait for government subsidized housing which strangely enough, places single males at the bottom of any waiting list, if they’re allowed at all.

    4.) So why ask why? In the tightest rental real estate market many cities have seen since WW11, we’ve got the now highly expensive ‘qualifier’ or requirement that the dude you’re dating come with his very own tastefully decorated home, (ready to occupy!) or at the very least a decent & Roomy apartment now? NYC is just now coming around to the ‘micro/mini’ trend in apartments with ~200 Sq ft. and it’s not too hard to find wildly overpriced but ever so dreary ‘minis’ @~400-500sq. ft units now. So which is preferable? The closet space you share with 1 plant & your pet lizard, which escapes every night to find more room, or your parents place where you might have your own entrance/bathroom & stovetop, instead of a glorified bucket/’eco friendly! composting toilet’ and a single hotplate & no closet space?

    5.) But hey, this is what it sounds like when doves cry. Nobody gives a hot damn. Or ever thinks about it much from the guy’s perspective. So what if you automatically toss out, what? Perhaps upwards of ~20% of the male population your age by eliminating such ‘losers’? Losers like the great Jazz player & composer John Coltrane who lived at home with his folks in Philly, even after he married, (to yes, his 1st wife). He only got his own place in the last 5 years of his life, dying at a young 40YO. That’s what the ‘tight rental market’ after WW11 looked like. It took decades to truly ‘clear’ before new affordable tract housing could be built, in a place they created especially for these middle class returning GI’s & service men their families, suburbia!

    6.) But damn the logic or reality here. So what if you’ve already racked up tons of ‘requirements’ your ‘serious’ dating prospects must possess. You know, the same <5% everyone else is running after. Some of the above advice is decent, keep positive, look sharp, apologize to no one, and know that you're likely helping your folks out more than you know. Still… this advice from Moxie is just, well, mostly wrong headed.

    Moxie says: "Your real priority here should be getting back on your feet. Maybe you should wait to date until you’re in a better financial position? Dating can be brutal on someone’s self-esteem. You already sound somewhat emotionally beaten down. Maybe put dating on the shelf a bit until you feel more settled?"

    7.) For generations it was fine for Both men & women to marry straight out of their parent's homes. Later it was often from a college dorm or frat/sorority house filled with friends & roommates. Then we got a bit more prosperous, and began to delay marriage until well after college graduation, (typically now, ~5+ years later). And so now we've created this new norm of 'having your own place' to nest, just to make some women you're dating more comfortable? Sorry, few places in the world, even the Western world, have these expensive requirements and somehow create the added 'needed conditions' for such wasted space and resources.

    8.) For literally generations guys & gals have lived with roommates or their parents before they were married. There simply was not enough housing stock, and it was overly expensive to do otherwise. Those days have now returned with a vengeance. We can deny reality all we want, and many might dearly desire to, especially when dating. But sadly NO, you defiantly should not put your life 'on hold' until you're 40 something when you might finally become more financially secure to buy/rent your own place. That might sound ever so attractive to some, but it's a trap to be avoided.

    Nothing much will be improved by postponing your life until you have the money to do what you want. It needs to be lived in the here & now with all that you've got now. Increasing age does not help much here, especially when trying to attract a mate. Think about it. Youth & health is the prize of the realm in dating. Even those ever so rich Hollywood moguls who finally 'settle down' to start a family at their advanced ages upon becoming fabulously wealthy, have a very limited time to be proper fathers to their children, or decent husbands to their wives. It was ever thus too. Almost everything you've got now will likely be working better sooner than later too! Cheers, 'VJ'

    • VJ Says:

      Yeah, real economics, yet another lost foreign world. So want to see what new families look like starting out? There’s some pics here from Slate. Couples in their bedrooms, sleeping. I count about 1 actual ‘Queen sized’ mattress in the group. The rest? Strangely enough look pretty damn typical from what I’ve seen of younger friends. The norm is almost slightly substandard. There’s plenty of less than adequate ‘bed sits’ out there, being endured somehow. And these young folks are trying the best they can for the sake of their new/growing families. The Pics are here from their ‘Behold’ photo blog:

      Now look at the rooms. Some look to be about the size & scope of SRO’s, but we can’t tell. What we can do is gauge the size of the beds & their set ups. That tells the tale. I imagine there’s plenty of women who’d turn up their noses at such ‘accommodations’. And there in tells a tale too. Too many rigorous requirements, and kids never get born, marriages are delayed until near reproductive senescence or don’t happen at all. That’s the economic reality here today. Deny it at your peril, but it can not be ignored. Cheers, ‘VJ’

    • AnnieNonymous Says:

      Moxie has said before that her “no roommate” rule is just one of her own requirements. She was pointing out that, unfairly or not, you can’t always use logic to work around other people’s standards. For someone dating in her age bracket, a man who doesn’t have his own place would be weird. Why would a man in his 40s or 50s still need a roommate? We’re talking a set of people that never had the student loan or employment issues that current 20- and 30-somethings do.

  6. DrivingMeNutes Says:

    Annie, I believe, hit the nail on the head up top. The advice suggests he try to play the part of the broke, divorced-guy who is buried with unfair support obligations when the evidence suggests he hasn’t earned that title. Seems more likely he was broke before he got married – not that the marriage caused his financial problems.

    • VJ Says:

      OK New Rule: Any dude broke/poor or un/under employed should not date. Now how silly does that sound? And would it ever be applied in the opposite manner? Likely not, eh? ‘VJ’

      • DrivingMeNutes Says:

        If you’re broke, you should date, but you need to come up with a plausible cover story. And, also one in the pocket for why you live with your parents. If it were me, I’d scrap the “the courts are so unfair to men!” and “It’s the economy, stupid!” lines and come up with something better. Maybe your parents are elderly and sick so you sold your mansion to move in with them?

      • AnnieNonymous Says:

        No one’s saying that men with money problems shouldn’t date, just that they shouldn’t be surprised if they’re rejected. Being able to date isn’t a birthright. Honestly, if you’re living with your parents at 32 and you don’t have a solid reason that’s mostly true, you have much bigger problems than who your next girlfriend is going to be.

        • mindstar Says:

          Certainly a good rule and one which would avoid certain problems however VJ makes a very good point. Would women agree to be held to the same standard?

          • AnnieNonymous Says:

            Well Moxie’s standard (a guy she seriously dates can’t have a roommate) is one that she adheres to herself. I don’t mind dating guys with roommates, since I have a roommate too. I probably wouldn’t date a guy who lived with his parents. So yes, women would enthusiastically agree to have their own standards applied to them. That’s why they have standards – to make sure they end up with an equal.

          • VJ Says:

            Again Reality Bites. And hard sometimes. About 1/3 of folks under the age of 35 live some time at home. That’s the reality today. Both sexes too. And this plays into one of the longest running arguments on this and other ‘dating’ blogs.

            Now OK, you’re oh so cute, ‘look 10-20 years younger’ than the competition, have your MA in Medieval English/Spanish Lit or an MSW or even a teaching Ed. and you’re constantly being told you’re a Hawt 30 something with ‘everything going on’ that Anyone would ‘want to get with’. The perfect prospect for the newly imagined landed gentry.

            What do you do? You immediately and Automatically then Dispose of the 1/3 of humanity you seek to date. And, again Reality Bites Harder. Because it’s not just ‘all those losers who live at home’, it’s often added to ‘all those losers who live with roommates’ too! Now do a Hazard statistical analysis here and you’ll come up with yes, another 10-20% automatically Disqualified on that errant requirement alone. Your granny might be appalled if you told her, your momma too! But now, you’ve already automatically disqualified upwards of 50% of the population, (depending on when you meet them) on those 2 points, alone.

            Obviously this is not good enough! But never mind, you’re great & in demand now! Educated, self sufficient, and don’t need anyone to ‘complete you’. But you still want them (dudes) to pick up the 1st check, and the one after that, and… Pretty soon you’re constantly working to whittle away your odds of ever being satisfied with mere available ‘mortals’. Only comic book heroes and media/movie stars need apply. And why not YOU as your own reality star? It could happen! You’re magnificent right now! You should want More! You Deserve better. Much better than what you’re seeing all around you.

            So to all of the above you add the ‘standard modern’ NYT/NYC ‘style weddings’ page requirements. Comes from a good/prosperous family. Stable & successful in their careers. All of them, but especially your prospective mate/date. Ivy league educated. Graduate education. Makes well over $100k or at least on ‘that trajectory’ if youngish. Tall. Always tall, athletic & healthy & ‘in shape’. Dark & handsome too. Easy on the eyes, kind, classy and dresses well too. Has an expensive car. And then everyone no doubt adds to the mix the regular BoyScout creed: He is Trustworthy, Loyal, Helpful, Friendly, Courteous, Kind, Obedient, Cheerful, Thrifty, Brave, Clean, and Reverent. ‘Stylish’ too!

            And you now arrive at the very same set of well under <5% of the population everyone else is chasing. And you're no doubt part of a 'harem' or 'in the rotation' if you're actually dating this magical man. And that's why you're still single too. You've already dispensed with too much of humanity well up in the decision chain/tree. But you knew that already too. And it'll never bother you. Even when alone. No one asks 'why not him'? when it's a poor schnook. They're always chasing after the bright shiny prospects of big money or imagined life long comfort. And therein lies the tale. And again too long, but yet another SSDD here! 'VJ'

    • D'Alias Says:

      I don’t see any evidence to suggest he’s “broke.” The assumption is quite a jump, we know nothing about his bills, education level (student debt?), consumer debt (and if it was for a good reason), etc. VJ’s got it right – many on here seem oblivious to financial reality for our generation. IDK, I’m 34 & the people I know who live “at home” include some Ivy League educated professionals, drs (young attendings), state troopers, NYPD, firemen, court officers, lawyers, social workers, production assistants, teachers, entrpeneurs, executive assistants, veterans, and, yes, some underemployed/unemployed people as well. I mean, if you eliminate ALL these people, who is left?

  7. wishing u well Says:

    OP – in addition to some of the feedback from above, do not underestimate the importance of your concerted, sincere, and consistent efforts to truly own your choices and move your life in a better direction. This is what needs to stand out in the minds of anyone you attempt to date. You may be living with parents right now, but what? Have you reduced debt significantly? Are you going back to school? I assume you’re employed full time. Have you started looking for a 2nd job to help bolster you back a higher level of expected independence? Have you started taking better care of your health – both mental and physical? Regardless of whether or not you have it together now – these things show potential. And there are many women who will align themselves with that. You want to get back to happy, that glint in your eye? Start with yourself. Bettering yourself improves life on many levels and increases overall confidence. And most women find confidence to be sexy.

    On the other hand, if you’re just enjoying a 2nd visit back to the teenage years with no game plan and no execution because you know your parents will never evict you or make you contribute to the household and you are taking advantage of the free ride: be prepared for the fact that many women will consider you undateable.

    What sticks out to me, OP, is that you trot out the divorce & living with parents without providing any other details about yourself that would provide a balanced picture of you. I wonder if you’ve been thrown back a loop due to life not meeting your initial expectations. If so, that’s okay. Consider this your opportunity to turn life’s lemons into lemonade. It’s hard but worth it. I wish you well.

  8. Bogey44 Says:

    I have to agree with VJ and some of the others. The financial realities facing many younger people now can make things pretty difficult and living at home or with roommates doesn’t necessarily equal broke loose. I’m 24 and I can’t even tell you how many people I know with college degrees, tremendous amounts of student loan debt, and who have been completely unable to find a job I’m their field. So they’re stuck waiting tables or something like that barely being able to cover their bills without even considering things like rent and utilities. There a lot of them and due to their numbers along its tough to lump them into “undateable” loser groups.

    That being said, we really don’t know what is finances were like before the divorce and how exactly the divorce impacted his current situation. The one thing that concerns me though is the, “I want to be happy again,”line. No woman, no matter how great she may be, can make you happy if you’re not, and taking that approach to dating well inevitably lead to more heartbreak and unhappiness. So my advice to the OP is similar to Moxie’s, figure out what it is YOU need to do to make YOURSELF happy. Do you want to get into better shape? Do you want to pursue a new hobby? Do you want to go back to school and change course in your career track? If so figure out a way to make those things happen. Additionally, use those avenues to meet women along the way rather than the online dating route. There are just too many options for women online for you to get your foot in the door if you aren’t exactly what their looking for. Lastly, if you haven’t already figure out what it is you need to do to better your situation and start executing your plan. You’re still at the age where you aren’t expected to have everything together so while success is attractive to women you’d be interested in dating the potential to become successful can be just as attractive.

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