I’m talking to a man I met IRL who seems like a good guy. He has told me that I’m beautiful and the whole package: I own my own business, good mother, nice house. So he was really taken aback when I said I’ve been single for so long. I got the impression that he was thinking that was a red flag.
The long break in dating was due to getting out of an 8 year long emotional and financially abusive relationship. Then a year later, my mother died after a failed bone marrow transplant. A year after that, I closed my salon and changed my business model to mobile. Then covid hit and everything shut down… except for mobile businesses. I paid my assistant to stay home for 3 months, so I worked alone. Then in September that year, 9 months after going mobile, my dad was killed on his motorcycle. All of this while being the solo mother of two kids.
Obviously, all of this is WAY WAY over sharing. I gave the usual vague answers, “I just haven’t met the right person yet”, “I needed time to work on myself”, “I’ve been too busy to date”. I did finally tell him that my last relationship ended badly, then both my parents passed away, but he still seemed almost… suspicious that I don’t have a dozen men chasing me and that I was so surprised when he called me beautiful.
Anyway, we were supposed to go bowling this afternoon, but now he just wants to see me for a little while between jobs and asked for a recent photo. Why? I look just like I did a week ago, what’s the point?
UPDATE: I told him we could do another night when he’s not working, but I’ve already written him off. One of my biggest icks is when someone I dont even know starts asking for pics. Or sending me a bunch of selfies. It’s cute when you’re in a relationship, but I really don’t like it otherwise.
50 comments
No. *Just* being single for x number of whatever is not a red flag. There are many reasons for being single. Anyone worth your time should care to explore which isn’t even always or even often necessary if you don’t present with some issues that would suggest there’s a reason why you were single that also applies to them. All this being said, it really does not matter. If you’re feeling off about the situation then that’s what you’re feeling. Why did he change plans? What does the new plan involve? I don’t know why he asked for the photo but I wouldn’t send it.
Honestly? The way he’s going about it and the fact he feels suspicious about people who can survive not being in a relationship are red flags on his end.
Not a red flag – have people forgotten that we’ve been in a pandemic for the past 2 years?
I’ve been single for 30 years so ¯\_(ツ)_/¯
I’d say he’s the red flag, not you. He probably thinks his words are endearing to you, otherwise I don’t know why any guy would be suspicious that dozens of guys are after you considering he infact is one of those said guys 😂. I’d personally tread lightly if I were you.
He’s acting like this all before bowling?!??
He’s already met you and is demanding another photo because you’ve been working and raising two kids?
Please do not send him anything other than a message saying you’re looking for different things and best of luck.
It’s a mystery where his head is at for me but he’s the thing that smells fishy. Not you.
I’m so sorry all this happened in such a short time.. must have been difficult for you.. you’re such a strong woman! I don’t know you but I’m proud of you and your kids are lucky to have a mom like you. If this guy isn’t impressed by your strength then he’s not worth it .
It just sounds like an akward way to tell you how high he values your attractiveness.
Wow, I’ve been single for 6-7 years and have not had nearly as many life-changing obstacles as you.
You are a trooper. Honestly, sometimes you need to handle all the fires life brings, before putting yourself out there. If he can’t understand that.. it’s his issue and loss.
I’d say him thinking it’s a red flag is a red flag.
There’s nothing wrong with being single for any amount of time, and you don’t need to give reasons why you were single. I’ve been single for many years. Longer than you! I enjoy being single and am in no hurry to get into a relationship.
I usually don’t tell guys how long I’ve been single anymore. I’ve had a few bad reactions too, and it always turns me off. As if the constant goal of everyone’s life is to be in a relationship.
No. Calling it a red flag is a total misjudgment. She may be taking time to heal, focusing on herself, preoccupied with her career and her education. Multiple reasons.
Weird. I got out of a 7 year relationship with a narcissist (two therapists diagnosed!) and I’ve been single for almost 3 years. I like my alone time now and would need somebody amazing to change that. I’d be concerned with anybody thinking that’s a red flag. It’s healthier to be able to be happy alone so when you’re with someone it’s because of mutual happiness and respect, not an inability to be alone.
People just wonder if you’re too picky, or maybe good at blowing up relationships. With your response, they don’t get an idea that this isn’t the case! Your response may not be ideal. It implies you’ve been looking when you haven’t! You’ve been dealing with massive, massive life stuff. I’d respond differently.
“Life challenges and building all this up with the pandemic took a lot more effort. I didn’t have time to date, honestly! Things have settled down now.”
It gives enough details without being an overshare. I get not wanting to talk about it all with a bunch of random strangers, so tell them it’s “stuff for a couple dates in, if you’re both feeling it.” for those who press. I wouldn’t worry much beyond that. Mature adults will understand and back off.
Been 6.5 years for me. Wondering the same.
I’m confused by the last bit. Why does he need a recent photo??
If it’s a red flag for someone, they must be a serial dater that leaps from one relationship straight to another and never gives themselves time to reflect on the previous relationship. Most likely not someone that you would want to date anyways.
No. It’s a better choice, actually. He’s had time to grieve and think about mistakes in his past relationships.
Did he say something other than he was surprised that you had been single for so long? Could you maybe have taken it the wrong way? You obviously will have time to get to know him and share with him as to why over time.
I don’t find it odd that he is asking for a photo to be honest. We scroll Facebook and Instagram daily looking at photos of other humans. He could possibly want to show a Co worker or friend your photo because he is excited to show who he is dating?!
I feel like a lot of times we take things way out of context because at our ages (35f widow) we have been through a lot in relationships and try to look for bad signs rather than good…
Also, you sound like an amazingly strong woman with a bright future and lucky kids to have such a strong mom! I am a single mom of two as well and successful. It’s a hard job but so rewarding at the end of the day! Go you 💛
It’s not a red flag unless you present it like one. 🙂
Also, how long one has been single should not be a first date conversation.
If I were you I would tell him you don’t want to meet him in between jobs and that you will go out with him when he has enough time to go on a proper date with you. I would also tell him you’re not going to send him a photo because he already knows what you look like. Sounds like he’s being a bit neggy and controlling
I’ve been single since February of 2018. Mostly because I decided after my relationship with my ex, I decided I wanted to be child free (I’m glad I never had kids with him. He would have only been the fun dad, while I did 200% of the work). I live in a rapidly growing Southern city, but all I would meet are men who want kids or are ‘open’ to kids (it means they want kids when their peers/friends start having kids.) So it hasn’t been fruitful.
But even in this 4 year time frame, I was able to buy a car, get a promotion, learn how to stretch a dollar, learn new skills, spend time developing friendships, invest in my passions and hobbies and get help for my mental health. But the best thing was narrowing down what qualities I look for in a partner and what are my values.
It’s been a ton of growth for me. It’s helped me become a better person and get closer to knowing what I want to do. I think it’s important that people make the time for self-improvement and hobby indulgence. Those who are serial monogamists are limiting themselves to how much development they can do. That’s more of a red flag, when they don’t go long without a partner or take time for themselves.
You can tell him.. “if today’s not a great day then we can meet another day when you’re more free, I prefer not to meet people when they’re in a rush or between jobs”
About the photo, you can say “ I’m not feeling like taking a photo right now, but when I do take a new photo I’ll share it with you.” if he really wants a photo to see you! Why not just see you in person ! 😅 doesn’t sound like a serious guy to me..
I’ve been single for nearly 5 years and honestly this sub is the closest I get to even considering dating. This idea that someone would care about that… no, their mind’s too closed off from the idea that people might have ACTUAL interesting and (subjectively) important issues to spend their time on.
I’m more alarmed by people who jump from one relationship to another. Being single for a few years tells me that their focus is elsewhere and there’s nothing wrong with that.
Not really no. You date when and who you want to date. You don’t owe anyone an explanation on your dating break.
If I were to meet someone who has been single for 4.5 years, well, that’s interesting. It _could_ be a reflection of her ability to form or maintain relationships, but I have no evidence of that. Has she been dating? Wanting to date? Doing other things? Has she been especially cautious about COVID? I am going to ask more questions because it might help me find out more about her. How does _she_ feel about it? Is she indifferent, glad, disappointed? And, if she wasn’t all that interested, what has changed in her life that she is more open now?
I don’t know what you do about this guy, or ones in the future, but I think it matters that he wasn’t curious. He (seemed to) go straight to suspicion. You felt a need to explain / defend, rather than an opportunity to share / enlighten. I get that you don’t want to dump all your stuff on him at once, but a normally curious person would likely learn that your parents both died, that you are divorced, that you transitioned your business just prior to the pandemic, without it being oversharing.
– Anyone who compliments you heavily on a surface thing (like appearance) before you’re properly dating is being manipulative at worst and superficial at best. Yellow/red flag.
– Anyone who gives you the “Oh, you’re so amazing. Why are you still single” really needs to work on his or her conversational skills.
– Anyone who gives you the impression that he or she is suspicious that you’re not being chased by a dozen prospects is a clumsy talker at best and insecure at worst. Yellow flag.
The guy sounds like a bit of a loser, to be honest.
As for your actual question – I would not hold a long period of being single against someone, as long as there was a subjectively good reason for it (working on myself/too busy with career/needed to heal/etc). If someone told me “I’ve been single for 4.5 years because I can’t attract anyone and I’m desperate for a date” then I’d be turned off, obviously.
If I start dating a woman who wants a relationship, I ask her relationship history. A long gap between relationships is a potential issue but the reason is important. Your situation would be no problem for me (and I’m truly sorry to hear all the hardships you’ve endured). However, his request for a photo after just meeting you in person is pretty weird. I would just ask him why he wants a photo and suggest getting together when he actually has time to do something with you.
I’ll give you insight to that mindset, with three thoughts that I used to believe:
It’s hard to believe that highly attractive potential partners are single by any reason other than choice.
It’s better to be in a relationship than not.
It’s hard to understand why someone who appears to have all the options available to them would choose the less desirable option for such a long period of time.
​
I’ve been like the guy the OP is talking to. I’ve been suspicious, but in a curious way, trying to understand why a potential partner was single for a while based on the three mental guidelines above.
Fortunately for me I’ve evolved a greater understanding of the choices people make in their lives. But I didn’t get there until well after I turned 30, so with a time machine, I could have been the one OP is talking about now. Many people don’t find the way until someone teaches them.
>asked for a recent photo. Why? I look just like I did a week ago, what’s the point?
I mean, you said he sounded suspicious so I’m gonna agree and think he’s asking because he thinks you’re cat fishing cuz clearly you must be ugly if you’ve been single, not that you have been by choice/are focusing on more important things.
You could just not respond. He could be joking, to give extreme benefit of doubt.
eta: Let me just say I also get extremely annoyed when dudes go “you must be such and such.” Like you’re showing your whole ass because now I know how you stereotype so-called beautiful women, or women my race, or women my age, etc etc etc.
And they’re usually wrong about it too.
No, especially if you have children. Taking time to work and yourself and heal before you enter a relationship with someone again is a superpower.
This guy is already making you question yourself. Don’t do it!
If this guy thinks it’s a red flag then HE is the red flag lol. Being in relationship after relationship is a red flag.
My boyfriend was single for 10 years before we got together
I took an 8 year break from dating and when I started again, I had a handful of men think it was weird, make crude comments, or tell me how much of my life I had wasted. But one guy told me “man, someone has been missing out on you.” From that point I’ve only looked for men with that energy and attitude.
This guy sounds like a jerk. Find you someone who respects your choices and you.
I hope not, I’ve been single for four years. 😅
I would just tell them you had a lot on your plate and dating at the time wasn’t the first thing you were interested in but now you are. The only reason I’ve been single as long as I have is if I see any red flag. I’m out before I even meet up in person.
Not a red flag at all. You were too busy and emotionally unavailable, and mature enough to recognize it.
I wouldn’t be suspicious. People stay single for a lot of reasons. Sounds like you’ve really been through a lot. Hugs if you want them. Good for you for prioritizing yourself, your children, and even being a stellar boss to your assistant!
He seems weird.
What’s not weird is being single.
It’s weird when you try and force relationships just to be in one. That’s a red flag.
You sound like a person who was able to save themselves from a crap relationship and didn’t rush into a new one….
Obviously- go with your gut. He seems like a weirdo – not the cool 😎 kind.
I’ve been single 7 years; first 3 I got a degree, then 1 year getting sober, then 1 year of dating and 2 years of a pandemic. Honestly time has flown and I can’t believe I’ve been single this long. I’ve been dating on and off for 6 years and haven’t had anything last longer than a few months. I’m older and wiser though, and want to find someone I’m compatible to have a healthy relationship with. I’m sure I could have gotten into a relationship in that time, if that were the end goal. But how many people do you know in your life that are really happy in their relationships? It’s worth waiting for that.
I find people fresh out of a relationship and dating again red flags. Some people don’t know how to be on their own and it leads to choosing people who aren’t right for them. Maybe he is intimidated by you being independent and strong enough to be without a man? If so, run.
Not a red flag at all (this is coming from a 40 year old guy).
I think it’s WAY more common for a woman, especially a single mom with a younger child, AND a business owner, to take time off to focus on other areas of life. Frankly I think this is part of the reason why men typically outnumber women on the apps – men leave one toe in the water, regardless of how ready they really are to date – while women will opt out of the dating pool entirely despite being reasonably on top of their lives.
I think that’s literally how I would translate the “I needed time to work on myself” comment – you were busy, focusing on other things. Guys don’t do that, so it’s foreign to them.
I’m going to make this easy for all the ladies out there:
Barring something so beyond the pale it’s obviously intolerable (physical violence, serious crimes … and sometimes even that sort of stuff is tolerated) there literally is NOTHING about you that will be a turn off to a guy if he finds you sufficiently attractive.
Oh, you’re a college drop-out virgin who’s financially struggling, hasn’t dated in 10 years, and you have crippling anxiety about going out in public? If he finds you sufficiently attractive he’ll gladly teach you how to smash and happily hang out with you inside with the curtains drawn for years on end.
Men just don’t have the sorts of “checklist to be worthy to date” like women sometimes seem to …
Its more of a flag to me to not be single more than a year or 2 at a time and having a string of exes. Being single is never a flag. It shows someone is comforrable, probably fairly secure, knows what they want and either just doesn’t want a relationship or hasn’t settled for one they don’t want. I’m also that person. After my last relationship which ended badly and major toxicity that left me pretty hurt and needing therapy, I am so much happier alone than i was with him, or the ex before him. I don’t need anyone, and will not take someone i’m not excited about.
Why is it suspicious that someone is single for a while? Some people think that there’s something wrong with you if you’re single and that mentality is terrible.
I think you’re totally awesome for waiting.
Why is he single? What about him????
I am happily single for the past 5 years now because I don’t base my happiness, health, or worth on having a man. Men tend to have issue with a woman who doesn’t NEED them but WANTS them. Idk, something about fragile masculinity. It’s scary for them.
I am 41 in the middle of a 3 year hiatus. Always had long term relationships (don’t do ons or fwb) and I was exhausted. I wouldn’t be single for 2 weeks and then it is another 5 years with a girlfriend. I hope that isn’t a red flag, I just needed space and time to think about myself and my wants. When you realize what you want you do not settle. when I was 18 I would jump, at 41 I do not waste my time with incompatible. I am not talking to people for sex, I want connection. That isn’t a red flag to me. That is someone who knows who they are.
Idk. I’m single going on eight years now, what kind of red flags are you thinking?
I’ve been side eyed for being single for a long time too, but I‘m a little skeptical of people who are hardly ever single… I have a hard time understand how people can “do the work” such as reflecting on what they’ve learned from past relationships and what they want in the future while constantly dating. However, everyone processes things differently, so maybe some people are capable of doing that. I just know I’m not! You sound like you’ve been through an incredible amount of trauma/life experiences and I also would’ve taken a break after those events (also just want to say that no one needs a reason to take a break, it’s okay to just not date if that’s what feels right for you).
4.5 years isn’t crazy at all, especially given COVID and especially the fact that you’re a single mother.
Skip this guy and look for the one who *appreciates* the fact that you took time off to heal/deal with your issues on your own first before dating.