I’ve (38M) been widowed for a number of years and started trying to date again this year. It is beyond depressing and stressful. What am I doing wrong?

24 comments

1. I was in a similar situation at about your age. I knew I wanted another relationship, but I was not meeting people, so I knew I had to actively put myself out there.

   This was before the Internet, so I was using a popular personals section in a local newspaper. I answered ads, I made a couple of ads, I had long phone calls with a few people, went on a couple of dates.

   I had to take detailed notes, both to know which people I had spoken to as well as personal details, my impressions, etc.

   This was HARD! For about every 30 people I spoke to I ended up with perhaps one qualified lead. This was a huge amount of work. It was also emotionally exhausting. It was a matter of several months before I ended up in a satisfactory LTR.

   So that’s my first piece of advice: don’t give up. It will take patience and time.

   My second recommendation is to spend a couple of sessions with a mental health professional. This whole process is dredging up a lot of ancient junk for you. You need a little time with someone to help you process and work through all this.

   Big hug, and good luck.

2. Try meeting people on the road?

   Also, you’re not alone in feeling this way – it’s popped up here before and I recall there being good advice. Try searching.

   Perhaps if you put developing friendships and new connections as the priority, then the right relationship will emerge.

3. Judging by the tone of your post, I sense a lot of negativity – lot of negative assumptions about yourself, about others, and about how others might perceive you. And that’s probably your biggest obstacle. When you feel exhausted, discouraged, and resentful, that negativity comes across.

   The way you talk to yourself is a self-fulfilling prophecy. You have to start there by challenging your self-talk and replacing it. When you catch yourself thinking something like, “Everyone is paired up. People are going to wonder why I’m single at my age and make assumptions,” you need to stop that train of thought and counter it with facts. You’re single at your age; why is it so hard to believe that there are women out there who are also in similar circumstances?

   Instead of going to bars and being miserable, try doing things you like – for yourself, first and foremost. Maybe that’s going to museums. Maybe that’s doing outdoorsy things. Maybe that’s running. Maybe that’s playing or watching sports. Can’t think of anything? Then maybe it’s time to try out a few new hobbies. The idea is that you start getting more enjoyment out of your free time, and, in the process, expanding your social circle. Don’t approach every activity you engage with a do-or-die mindset, “If I don’t meet an eligible woman who seems interested in me at this particular venue today, then this is a pointless waste of time, so I give up.”

   Being on the road a lot doesn’t have to be lonely. It gives you lots of opportunities to cross paths with people you otherwise wouldn’t in your medium-to-large sized town.

   Relax a little, fixate less on your relationship status, try to have more fun in your day-to-day life, and be open to the possibilities that life puts in your path.

4. I’m sorry what you are going through. The dating scene has truly changed in the last decade. I’d recommend changing up your routines, just expanding your social circle a lot and find organic situations to find dates.

5. Online dating is not for everyone! Have you got any hobbies? That’s a good way to meet new people. Try new activities, push yourself to talk to people in real life rather than swiping on your phone

6. When I was widowed, I did the online dating thing and I started going to every meetup group and event I thought I might like. Fortunately, my now husband did the same. He was also widowed and the age you are now. We met at a meetup event foe a young widowed group I ran at the time.

   Having met my first husband in college before social media, then dating again after the creation of dating apps, there was a big learning curve. I’m a woman, so my experience is obviously going to be different than yours, but I found much better relationships, platonic and romantic, by doing activities I liked.

7. What would help would be to enlarge your social circle. Sometimes when we have too many expectations, if we fail them, we feel like a loser. But we just have to adjust the expectations to reality and what is right for us.
   Maybe you should expect to just meet people (not future partners in itself) to maybe become friends and to gain confidence in yourself first.
   I would not try that in bars when you are alone as I think the setting is not always the funniest and doesn’t seem to fit you.
   Do you sometimes have social gatherings at work?
   Do you have any hobbies or do you make some sport ?
   Even though you are traveling a lot, there must be something something that you like that you could do while on the roads too/in every cities you visit.
   Guided visits in museums.
   Birds watching or walking in nature with other people.
   Going to the gym.
   Going to the theater.

   I’m single too and I tend to be sometimes too introverted. So I also decided to embrace :
   Solo times, Going to group activities alone and value friendships. I can ask for affection from my friends first. That way I can feel at ease and learn to speak more about my thoughts and feelings. I keep contact with them everyday to get out of my comfort zone.

8. So I’m a woman and you definitely don’t want to go to the bar to meet women not the right atmosphere to find someone that you want to settle down with. I recommend putting yourself in the right environments to meet the right woman I’m not sure if you are religious but you can go to church groups to meet people there’s also a website/app called meetup where you can do fun activities and meet people around your age group. They have groups for everything, hiking, bike riding book clubs, karaoke people watch sports games there as well. I think this would help you out a lot better than a dating app. Good luck to you and don’t give up!

9. Personally, I think being up front about being a widower should be something to lean into. You can’t escape it and you won’t really be able to create any emotional intimacy with someone if you try to. You definitely can draw boundaries early on, like you don’t have to go into a lot of detail, but the point of dating is getting to know the other person. I understand that it’s not a fun thing to talk about with dates, and how a date handles the subject might be condescending or just make you feel bad. But it’s who you are and I think if you look at it as a compatibility thing, as in does your date’s handling of it jive with you, rather than looking at it as being a damned if you do, damned if you don’t situation, might make it more palatable. Like, maybe for a first date, set the boundaries at just the very generic facts. Like, something as simple as your first line of this post, what happened and when is enough, followed by a “But it’s a subject I don’t really enjoy diving into on a first date, I hope you understand.” I know it’s easy for me to say all of this, I’m not in your shoes with the real feelings you have about this, but that’s my 2c.

   My only other advice is to invest as much into yourself, in terms of time and energy, as you do with dating. It sounds like you’re doing well with work, which is a great place to focus. But, investing in things like your health and hobbies and interests are as important as doing well at work and finding romantic companionship. And those investments in yourself will help your mood when dating feels depressing. And try to find a way to incorporate it into your business travels, so you have more to do during your downtime when traveling for work. It will help your romantic life as well, you’ll be more confident, happy and interesting, which will make you more attractive and less invisible. It almost doesn’t matter what you choose to do, just make sure it’s something will make you proud of yourself.

10. >If I let it out and be honest that I am widowed, women treat me like I’m some sort of abandoned puppy or something. They just want to talk about that whole situation, and to be honest I am so tired of talking about it and want to move on and let her memory occupy my own personal spot in my mind.

    This threw me a bit. I can understand not wanting to be excessively fawned over or treated like an emotional fixer-upper on account of your widowhood, but the majority of women you meet are likely to respond to the news of your wife’s death with condolences. I realize that can feel awkward and that you’re tired of having the conversation, but I’m also not sure what other response you’re hoping for, and I think you might be prematurely ruling out some cool women as a result.

11. The thing about your previous partner is that every woman you meet is going to ask a few questions. I know that it’s in your past, but it’s still a very important part of life.

    I personally would ask questions to gauge how that relationship was. Not out of curiosity, but rather to learn about you. Obviously this shouldn’t be the bulk of the talk, but it’s going to be hard not to discuss this with a future partner. It helps them understand more.

    I’m 35 and find this entire dating thing daunting. I get that. Keep trying though. You just have to find the right person where all of this feels right. Easier.

    You’ll get there.

12. I can’t wait for the day I see you post again saying you found someone new! Remember, There is someone for everyone! put yourself out there with a positive mind and attitude and you’ll be able to see the good in life. Best of luck to you!

13. This is going to sound like a flippant comment, but I found it encouraging when I was looking:

    It only takes one.

    Even if you talk with 99 duds and one winner, the only thing that matters is the winner. My brother-in-law met his wife through someone he went on a date with – they enjoyed each other’s company, but there was no chemistry, so this woman set him up with his now wife. Who knows what will happen.

    And as for bringing up your past, it is okay to say, “I have been married, but let’s not talk about past relationships until we know each other a little better”. A respectful woman will honour that.

    The other thing I would suggest is to throw yourself into something you LOVE to do on the weeks when you’re in town. Golf, the tango, astronomy club, or whatever floats your boat. There are a million ways to enjoy life, and this will make you naturally more attractive to the type of woman you want to spend time with.

14. I know this isn’t the best advice, but all I can say is just keep going. Keep living your life, keep spending time with friends, keep doing all the things you love to do, even keep online dating to meet new people. Loneliness is so difficult to go through, but you have to continue to find meaning in your life for what it is right now. I’ve never lost a SO, so I’m not even going to try and understand what you’ve been through, but I have been lonely in life at times and it’s really hard. I decided to embrace being by myself and “living my best life” without anyone else to consider. I also kept online dating and meeting new people. It was fun to meet people I lived within 5 miles of and would have never met before. It can get tiresome and discouraging tho, especially for an introvert like me, and when it seems like you’ll never meet the right person. I was about to delete the Bumble app to take a break from it when I decided to give it one more try with this one guy. 2 years later we are still going strong 😊 My very long-winded point is, just keep living your life, embrace the solitude of being by yourself, curate a life you love by yourself, and have faith that you will find love and companionship again. It will happen, but don’t put your happiness on hold waiting for someone else. Enjoy your life now and find the beauty in it just as it is.

15. i am 11 please do not sned me emails

16. I was widowed at 41 (48F now) and it’s hard. Sometimes I just say I’ve been single for a few years and explain after a date or two and sometimes I’m up front about it. It often depends on how open I feel when asked.

    It took me about two or three years before I wanted to date. Partly because I was learning how to be by myself and partly because I just wasn’t interested in anyone. Best advice is to give yourself grace. Online dating sucks and it’s hard to tell what real and what’s not. If you get stood up- treat yourself since you’re already out! Self care matters. And good luck- I wish I had better advice but I’m still dipping my toes in and out of the pool 😉

17. You’re being way too hard on yourself. You said you’re working on yourself so I assume you must be working out, taking care of your appearance, etc. Honestly perhaps have a close friend look at your dating profile and pump it up a bit. You could be underselling yourself.

18. Hey, I’m also widowed and tried to date afterwards. Just couldn’t find someone that was a good fit for me.

    So I became abstinent, and been abstinent for three years.

    I’m not opposed to sex or dating, but I decided to stop seeking it out

    I didn’t seek out my late husband, we met naturally and got together.

    After he passed away I had tried to “date” in a more forceful “looking” way. I never found anyone that was right for me.

    I decided that it will happen when it happens and just decide to work on myself, my life, my hobbies, making friends and ect.

    I was widowed very young, at 25, and most people said I should “find” another person and have a family. Well I tried to “find” someone and it just doesn’t work well with me.

    I’ve come close to finding people naturally and it has come close but there is always something about them that they shouldn’t have to change about themselves to be with me so I stop engaging.

    I’m happy where I’m at. At first it was hard being abstinent, but it got easier and I was a lot safer in doing so.

    If I feel like I want sex, I just fantasize or masturbate. I can’t just meet someone and start a loving and respectful relationship, it takes time to get to know someone, it takes time to find out their inner workings, flaws, benefits, personality, compatibility, life goals, shared life goals.

    Try to begin a relationship with yourself. Start trying to be ok with just having your own company for a couple years with out activity seeking a partner.

    If you find someone during that time then that is great, if you don’t you learn to be able to enjoy your own presence without pining over a relationship.

    I’m sorry you lost your loved one.. I know exactly what it is like to have lost a partner so young.

19. Go to a gym. You’ll get healthier, better looking and have more energy. Plus, you might meet someone or someone who has a friend who is also a great catch. Don’t focus so much on finding a relationship. Besides, it’ll likely come when you least expect it.

    There’s an old saying, “A watched pot never boils.”

20. Get therapy to deal with your negative outlook.

    If you want to get married again at your age, strongly consider looking overseas.

21. I read the whole thread. It feels like you’ve already given up, and if that’s the attitude you have you’re never going to get anywhere. The first thing you’ve gotta fix is your outlook. I understand that life dealt you a tough hand but you’re still relatively young. There’s no reason to feel like you can’t live a fulfilling live from here on out with a partner by your side.

22. I’m 30F single and most of my single friends have been hitting roadblocks.

    I think the dating scene has changed so much and lockdown didn’t help people making social connections easily. It’s almost like people forgot how to connect.

    When I match with men I feel I’m carrying the conversation as well.

    I am going to try speed dating in my city to see if that sparks something.

    I sympathize and I don’t think you’re doing anything wrong. I know how lonely and frustrating it can be when you want love and feel ready for it but it seems to not exists for you.
    It’s just quite literally finding a needle in a haystack.

    I wish and all the singles out there love !

23. I’m sorry for your loss and experience. Dating these days is already hard in general for everyone 🙁

24. I’m also a widow in my 30s (2 years out), and that’s why I say this with kindness and understanding: you’re letting your depressed brain f*ck you over with the negative self talk. I’m sorry if that is harsh, but it’s the truth.

    People are giving you great suggestions for ways to find community and friends, and eventually maybe companionship, and you are shooting everything down with excuses why it won’t work. You *can* join meetup groups in your local area or while travelling even if you are away half the month, nobody will care. You can join Couchsurfing, Airbnb or Facebook meetups to meet other travellers while travelling, I’ve had dinner with people around the world through groups like that. It isn’t unethical to start something up with a woman even if you are only in a location for a week, people do short term hookups or casual dates all the time. You can make friends with people who are married, and primarily be friends with one partner and not be a third wheel. There are long term single people your age out there who need friends, but it takes time to find them. Yes, your best friend and life partner died – but that doesn’t mean you will always feel as lonely as you do now. And we are actually a lot of people out there who understand how you feel, because it is our lived reality too.

    Research shows that the best protection against depression and loneliness is a strong social network, and you sound unwilling to invest in developing a new network that suits your current needs outside of dating. I don’t know if that is actually the case, but it’s how it comes across here. You’ve shot down every suggestion to start investing in making new friends, or you turn it into “but friends won’t get me dates”. Getting dates isn’t the point of making new friends, the point of making new friends is to have people who understand you to lean on to be less lonely and depressed. I’ve spent the better part of 1,5 years building up a new social network from scratch in a new, small city after being widowed, to make friends that are in similar life situations to me, are single, or understand life with trauma. Because I refuse to be lonely, even if I am alone. I especially refuse to feel lonely among friends.

    Lastly, you’ve only been dating for seven months. It’s not even been a year. Telling you to give up now and that it is hopeless is your depression’s way of trying to protect you from hurt. But you are still, by all measures, incredibly new to the dating game. I was single for a decade before I met my late partner, and dating for several years before meeting someone is normal. Dating is shitty and hard, but in order for it not to break you, you have to learn to build yourself up instead of letting your brain tear your down when it is hard.

    Again, I want to reiterate that I say this harshly but with love. Your brain is messing things up by lying to you about reality (“Me sitting in this hotel room alone means reality is I’m hopeless”), by practicing black/white thinking (“it’s immediate success or it will never happen”), absolutist thinking (“I will always feel this way”), and trying to protect you by pulling you away from you efforts with a myriad of excuses (see second paragraph for many of the ones your brain has made). I suggest talking to your therapist about this, about how to work on the negative self talk and urge to withdraw. Because your brain is making things worse, and that’s depression in a nutshell.