The Never-Had-A-Boyfriend Red Flag

14 Jul

If you read this blog regularly (which I admit is difficult since I don’t update it regularly), you’ve probably figured out that I haven’t had a boyfriend since I started it. If you know me personally, you probably know that I’ve never actually had a boyfriend. At least, not a serious one. I’m certainly an expert at first and second dates and I’ve had a few guys for whom I’ve had feelings of a relatively serious nature and sometimes those feelings have even been mutual! But I’ve never referred to a guy as my boyfriend and while I refer to several people in my past as “guys I’ve dated,” I don’t have any exes.

For the most part, I’m ok with this. At 16, when I hadn’t so much as kissed a boy, I thought something was wrong with me. At 21, when I’d nearly completed college entirely single and had yet to have sex for the first time, I questioned myself. For the first few years after college, I wondered why no one wanted to date me. I wondered what was still wrong with me that I hadn’t had a boyfriend yet.

Now, at 26, I’m ready for a relationship and I’m having some issues finding one. But I’ve come a long way in the last 10 years and I’ve finally realized that not having had a serious relationship – yet – doesn’t mean anything. It’s been a while since I’ve had any pangs of that gut-wrenching insecurity that makes me question myself – that makes me wonder, What’s wrong with me?

Yesterday, I read this post about how only you can make yourself happy. How a relationship – romantic or any other – doesn’t have the power to give you the security and the happiness that you want and deserve. As I read it, I felt like I was reading my own thoughts on the same topic – minus the painful breakup. I considered myself lucky to have learned that lesson without having to go through heartache.

Then, after dinner with my mom last night, we were standing in Union Square, not yet done chatting for the night. My mom was telling me about her close friend, Patti, who’s “not in a good place.” At 45, Patti is a bit younger than my mom, divorced and single, and really frustrated with it. Patti has a lot of hangups and unreasonable standards; she also doesn’t want to date any widowers, though she’s ok with divorced men. I made a comment to my mom that it sounded like Patti would prefer the unrealistic ideal of, at 45, finding a man who had never been married, employed people to do things he could do himself, and didn’t own a pair of flip-flops. I laughed about it with my mom until she said:

“If I met a man who’d never been married by 45, that would be a huge red flag. Clearly something is wrong with him.”

Suddenly, the tone shifted. Why, I asked, was this a red flag? What exactly does it say about a man if he has not yet made a lifetime commitment to a woman? Wouldn’t it be worse if he’d taken the vows and then broken them?

“Well, ok,” my mom backtracked a bit. “As long as he’s had long-term, serious relationships, then that’s fine. I guess he wouldn’t have to have been married.”

But I pushed further.

“What if,” I asked, “the man in question kept meeting women with the intent of forming a serious relationship and, after several months, realized it was not going where he wanted? Should he stay in the relationship for a year and a half for the sake of being able to say he’s had a long-term, serious relationship?”

My mom looked taken aback. I’d brought up a point she’d clearly never considered; I even surprised myself as I continued:

“At what age does it become a red flag, anyway? By 30? 45? Does never having had a serious relationship make a man – or anyone – less worthy of having one at all?”

A look came over my mom’s face that appeared to be a mix of confusion and also sudden understanding. She’d walked into a minefield: Her 26-year-old daughter has never had a serious relationship and she’s just been declaring that a red flag for men (and people) over a certain age. Well, shit.

I was getting a little worked up and we were on the corner of 14th street, so it wasn’t the place to continue the discussion. But last night, for the first time in a very long time, I was riddled with insecurity and doubt. I found myself lying in bed questioning what could possibly be wrong with me that I am well on my way to embodying this Giant Red Flag called Never Been in a Serious Relationship. It occurred to me the way I figured out that I have to make myself happy before I can let someone else into my life – without actually letting someone into my life – was wrong.

The no-boyfriend-insecurity is something I’ve worked really hard on overcoming, but it’s a fragile triumph (clearly). I wonder –  if everyone has to start somewhere, at what point is it considered too late to start? And what then? I’ll be 27 in a little over two months and even if at that point I’ve met a great guy I really like, it won’t be serious at that point. Is my Red Flag growing bigger, then? Am I less worthy of a committed, serious relationship – something I very much want eventually – because I’ve never had one?

I guess my real question is: Since when did long-term relationships become pre-requisites for long-term relationships?


23 Responses to “The Never-Had-A-Boyfriend Red Flag”

  1. earthtoadam July 14, 2011 at 10:48 am #

    Additionally… what length of relationship qualified a long-term relationship? Is length of relationship more important than quality and depth? That is to say, is a deep, loving year long relationship less valid or significant than a 5 year relationship that doesn’t incite deep passion, but is built out of contentment?

    I think that a sense of self-awareness is most important when going into a long-term relationship rather than any relationship history.

  2. Nick July 14, 2011 at 11:04 am #

    I think a lot of the “need a long-term to have a long-term” idea is just based on experience. The more you do something, the better you are at it. I view a lot of my past (and therefore, in a fashion, failed) relationships as learning experiences that teach you more for the next relationship. And I think a lot of people see having had a long-term relationship as an indicator that you are willing to commit, able to be with someone for a long time, and all the other fluffy things that come out of being in a relationship. Honestly, most of what you learn in a relationship is more about yourself rather than the skill of having a relationship. Of course, these things won’t show things like “Didn’t have the spine to end it” or “Nothing else seemed better” or “Security > happiness” fallacies that all too often arise in ‘long-term relationships’. There is some degree of truth to ‘if you have had experience in LT relationships you might be better at LT relationships’, but I don’t think that experience is any better (by any stretch) than the more important factor of being compatible with your significant other.
    Some people just get it right the first time. I wont embarrass any of my friends here, but I have several that have only had one truly serious relationship, and they have never balked from that and appear to be perfectly content. There are others that have had multiple serious relationships and they are more confused than anyone else about what they want and expect out of a SO.
    I think Dr. Dre’s comment about a 45-year old man is a fair one though. 45 is a lot of years to have never claimed to have been in a serious relationship- what changed in all that time that you are seeking one now? Or if he has been seeking one in all that time, why is that he didn’t find anyone? Maybe his standards were unapproachable by anyone human.
    These thoughts havent been well organized but the point Im trying to make is simply this:
    People see long term relationships as an indicator that you are capable of having long term relationships. This is clearly not the case very often (hell, if anything, people that have had long term relationships clearly failed at them otherwise they wouldnt be single now). You (and anyone else not having had an LTR) are just as capable of having and LTR as anyone else, because it will mostly succeed based on you as a person and your SO as a person, much more so than any ‘experience’ with it.

  3. marriagecoach1 July 14, 2011 at 4:06 pm #

    Well I suspect that you have not had a boyfriend because you really don’t want one. Do I remember previous posts where you confessed being bi?

    If you really want a boyfriend, it is not all that hard really. You can get on internet dating sites. You can smile at a guy and if he does not come over andintroduce himself, you can playfully call out to him and ask him, “Are you going to come over here and talk to me or am I too ugly”? Not that you are ugly, but it is a humorous approach that breaks the ice.

    Blessings on you and yours

  4. Carmen July 14, 2011 at 4:43 pm #

    I am in the same boat. I will be 31 in less than a month and I have not yet had a serious relationship or found mutual love. I have been dating someone for 13 months but he has said several times that it is not serious (and just recently that he’s not in love). I can’t say I have any real words of advice…. but know that you’re not alone in your situation. Also, I do not believe that the amount of time spent in a relationship has alot to do with the level of serious-ness.. lol. I am afraid I have too many flaws for a man to fall in love with me.. but I want to believe that we are not less worthy of a serious relationship because we haven’t had one by a certain birthday.

  5. sgba July 14, 2011 at 10:25 pm #

    @ earthtoadam & nick – You guys bring up really valid and insightful points! Thanks!
    @ marriagecoach – I appreciate the comment; I’m definitely not bi nor have I ever seriously questioned my sexual orientation. Not sure which post you’re thinking of! I do actively pursue dates and have been on many – I do think my specific, current singledom is more a product of my location (NYC) than any other factor right now.
    @ Carmen – I don’t know you, but I am very certain you do not have too many flaws for a man to fall in love with you! If a serious relationship is what you want then you deserve to pursue that. Don’t settle for someone who negates over a year of dating by saying it’s not serious!

  6. hijabeng July 19, 2011 at 2:03 pm #

    Ugh, I agree with you so much it hurts. Except in our community, you’re somehow supposed to be this superchaste person who doesn’t date but somehow gets married before 25. Really, this whole dating/marriage/serious relationship thing makes me hate people.

  7. Merrick July 23, 2011 at 10:49 pm #

    I have a friend who is 42 and has never been in a serious relationship. Not because he doesn’t want one, just because he hasn’t found his significant other (I personally do not believe in soul-mates but rather compatible partners, of which every person has thousands). If you want a relationship you’ll get one, and yes maybe you have to lower your standards and accept a 45 year old widow or whatever. Why does that matter? If the person fits well with you then nothing really matters. But a lot of people do the wrong thing when trying to find a partner. They should just STOP LOOKING, the best relationships happen out of spontaneity. So should you do nothing? NO, you need to expand your horizons, go try new things and meet people. Maybe you should think about leaving NYC, or even the country. Go overseas as this instantly makes you different to everyone else. And you’ll get noticed more, and be in more of a high-demand.

    There’s a quote that I live by : “though no-one can go back and make a brand new start, anyone can start from now to make a brand new ending.” and “The only person who doesn’t make mistakes, is the person who doesn’t do anything.”

    You don’t need love or a family to feel awesome, but it does help. I’m 22, and I have no idea what I want to do with my life exactly. I just came out of a 3 year relationship, and honestly its a breath of fresh air. Having only my own responsibilities is excellent. But still, I feel the innate need to procreate that has kept us humans alive forever. I want children, I want a loving wife, I don’t want a white house with blue shutters and a tire swing but would rather a unique house and a sports car haha. Life is tricky, but if you want something then go and get it because no-one is gonna get it for you. Mr. Perfect might just walk through the door, but its highly unlikely. Mr. Alright who’s faults and flaws keep things fresh and interesting is waiting just outside the door. But you have to find him, and you do that by getting out of your comfort zone. If you want change, you first must change.

    You asked: Since when did long-term relationships become pre-requisites for long-term relationships?
    They never ever were, and never ever will be.

    I also want to point out that the world is full of unhappy married/De facto people. It could take another 10 years to find your partner. But just enjoy the journey, life is the most amazing thing. As for me, I’m going to be the best guy I can be and hopefully Miss Alright is just around the corner…

    Hope this helps. -Merrick

  8. Noname July 31, 2011 at 11:30 am #

    What’s more of a ” red flag”? A person who is 25 and over yet never had a boy/girlfriend? Or the person who is 25, been in a 3 year relationship with two kids and a baby momma? Or is it the individuals whos been divorced by 30? Or the guy thats just gotten out of a 2 year relationship with the “love of his life,” who he should have married and now he’s compairing every chick he dates to “her” ( the love of his life)?

    I say red flags are people who date and sleep around but don’t commit, people with a whole bunch of children, cheaters. If you’re a virgin and have never had a serious relationship then I just see you as a person that may have some kind of trouble relating to me men, or shy.

  9. Noname July 31, 2011 at 11:40 am #

    What I was trying to say above was, there are a lot of confused single people who have been in long term relationships. Sometimes people who have been in a long term and are now on the dating scene have a lot of baggage from their other relationships. I would rather date a guy who is 4o year old virgin than a 40 year old man whos been divorced.

  10. Tom August 24, 2011 at 10:38 am #

    Of course it is a red flag, mainly because of the many questions that arise from it: does this person have unrealistically high standards? Does he or she have some character flaws like selfishness, agressiveness or something similar that kept people from building a true long-term relationship with that person?
    And these questions actually do come up even faster when you confess to have been on many dates, as opposed to being a shy person who would not dare to ask anyone out for fear of rejection

  11. Debster October 10, 2011 at 11:04 pm #

    @ Tom and anyone else who view those never being ina long term relationship as messed up…you could be right. And you can project “wrongness” on the person if you want. Perhaps it would be more compassionate to consider they have had a lifetime of abuse….and although wanted relationships…were in constant contact with humans that do the very thing you are saying they do…selfishness, unreasonableness, aggressiveness. Blaming the person because they decided to not let anyone get close isnt the answer. For me, trust has been severely impacted.

  12. Valentin October 13, 2011 at 8:08 pm #

    This is a great example of what judgmental bitches most women are. This is why more and more men just don’t bother with you anymore and you wonder “awww why don’t I have a boyfriend I’m so great”. Maybe if you were more humble and not such total bitches you’d have better luck.

  13. dee January 23, 2012 at 7:17 am #

    Oh my goodness. I’m 21 and I’m already thinking about this. Although to be honest I know what holds me back from letting myself have a serious relationship. I would like to be the best me possible/ unconditionally love myself/gain confidence before having a relationship.

  14. tobyyy March 20, 2012 at 1:44 am #

    hey guys, im 22 and find myself in the position where I am wanting a relationship. I’ve had one boyfriend/serious relationship for a little over 3 years and since we’ve called it quits I’ve had no desire to really be with anyone else (until now). Ive had opportunities to engage in other serious relationships but I havent simply because I wasnt completely over my ex. He scarred me in a way i deemed unimaginable and until i was fully over the pain i remained to myself. Mentally isolated from the thought of pursuing someone else….its been about 3 years since we’ve broke up and Im JUST NOW starting to come around and feel like myself again. i dont deal with break ups easily (as you can see) and as bad as I want to be in a relationship now a huge part of me is still afraid of being hurt again. Although I feel like this time around I’d much better be able to handle it I dont know if its something id ever want to go through again. Im such a wuss!! In between time though while being single Ive taken the time to really learn myself in a way in which i understand where I went wrong and can improve when in a relationship. I feel like im ready…but i have a tendency to overthink shit and its aggravating as hell. People ask me why im single and Im lowkey embarrassed to tell them the real reason, which is “ohh im not fullly over my breakup from 3 yrs agooo” they’d certainly tell me to get a grip lols. Its tough though (well for me) that was my first “real” relationship..hell… my only and it ended miserably, of course thats going to affect me in a somewhat negative way. The way I view relationships is that they are scaryy lols but I know this fear is really all in my head. Every guy isnt my last and i know this its just hard for me to let love in and trust again without realizing im now exposing myself to that type of hurt again. My problem is im trying to save myself from a heartbreak that hasnt happened yet, playing it wayyyy too safe. Im sick of it! i need to be more of a risk taker…I want to share my life with someone who I truly adore. Someone who im compatible with and who can respect me and appreciate me for me (corny) but its true and I WILL GET IT. Not looking for it either..I believe the LAW OF ATTRACTION is real and I just spoke it into existence…

  15. T.L April 11, 2012 at 6:16 am #

    I am also 26 and have never had a boyfriend, and not for lack of trying. I have been on quite a few dating sites over the years and just never seem to find anyone who wants to date me. I am fairly outgoing and gregarious; and I have many friends. I meet people a lot of the time but they never really seem very interested in me. There is nothing wrong with my looks or personality; but honestly I seen women with less than stellar looks or personalities find boyfriends. I also live in NYC where it’s pretty darn difficult to find love. It makes me search within myself to see what is wrong with me; and at the same time I wonder if I should just find a different city to live in so I can have a better chance. In the meantime, I am not sitting around waiting for anyone; and I try everyday to live life for myself and find other things that will make me happy.

  16. Jack May 12, 2012 at 12:36 pm #

    Let’s start with what the purpose of a relationship is. The very first, and most important for some, is for the continuation of the species…procreation. If you are not interested in having children, then there is no reason to rush into a relationship, simply because you have different priorities. Which is totally fine!

    The second reason people enter into a relationship is for companionship, as well as support. Our culture has propagated that myth of true love (think Disney), which doesn’t exist. After the initial rush of new love, most people settle into a more consummate love relationship, which is punctuated by trust, intimacy, and commitment. Additionally, as one gets older, we tend to weed out the people that bring us down, and increase relationships with people we actually like. Another point is how our culture has trained men and women to act. Men never discuss emotions, and women give emotional support. With all of this said, if you get emotional support and companionship from others, then you are less likely to look for it in a serious relationship. Again, this is totally fine. You may find, however, that as you age, you’re closest of friends will enter into serious relationships, and consequently devote less time to you, shrinking your inner circle of trusted confidants. Chances are, this will cause you to reevaluate your situation, and may propel you into finding someone, anyone, to fill that void.

    Dating is to learn about potential mates…be it for reproduction, or companionship. Either way, dating, like life, is a learning experience. A relationship is much like learning to play and instrument. The more you practice, the better you become for the performance.

    On the other hand, a relationship teaches us how to get along with others. If you have ever lived with someone other than family, then you understand the complicated “dance” that is required for harmony. The difference between friends and a significant other is that it requires the “us” mentality. However, with the lost autonomy comes the assurance and steadfastness of a strong base.

    One final point. Your decision to remain relatively single is based on the unconscious assumption that you will live to a ripe, old age. I can tell you that life is short, and there are no guarantees. You could get hit by a bus tomorrow. Whatever you decide will be right for you. However, try to relish life for today. Value those that you have now. This time will never come again. And if you meet someone that makes you happy and treats you right, like a precious stone, grab ahold and enjoy it for what it is, for that person will never come again.

  17. K.K December 7, 2012 at 4:21 pm #


    Sometimes, it all boils down to luck.

    Let me give you my own example:I am a 32-years-old woman (looks – OK, I’m guessing).
    I have travelled extensively, have lived in England, Ireland, the USA, France, Italy, Eastern Europe. I speak a few languages, have various hobbies, including salsa dancing, which is incredibly sociable; I work in a IT company, where the ratio of men to women is 5:1. Still, I haven’t met my SO.

    I also have a good female friend, who was my roommate at university. She rarely went out, but on one of the few occasions when she did, she met a great guy, who is now her husband.

  18. renee March 2, 2013 at 11:08 pm #

    Wow… I’m in the exact same boat, I’m 26 and have only just started opening to the idea of a relationship… Some just take a little longer to move along and in this instance, I’m one of them. I am however unashamedly one of them and I loved everything you stated in the beginning of your blog :).
    In regards to when does long term relationships become pre reqs for long term relationships…. I’m taking the boring road and going with we all have our journeys, who’s to judge?

    And in regards to age, everyone I know has their own idea of the dreaded number where after you reach it, skin sags, wrinkles mould way too comfortably and we’re near date of expiry. I travel constantly for work and have found that those who see anything over 25 as…. Getting there lol. However those who are more out there in general and more open in character, sometimes mind don’t have that restriction.. I gained confidence in them and (with work) dropped the waste of energy used in engaging with my insecurities…

    Anyway, just adding my bit :D. You sound like you’re doing great work with your insecurities, good for you and keep writing the good blogs

  19. Lina March 16, 2013 at 10:01 pm #

    If you really wanted a boyfriend, you would have found one by now. Forget excuses and open yourself up to a new relationship.

  20. Elle April 1, 2013 at 7:35 pm #

    I am 29 and have had 2 serious relationships, in college,and one really long non-relationship for. I would have to say that it would be really nice to have someone to love me but I realized that I can’t wait on that. You will start to internalize that and really beat yourself up, thinking its your fault for not being “available
    . The fact that I am single, no kids lets me know that everything happens in due time. So I try not to beat myself up about it and have really began to try to change my social circle. All I can do is hope and pray! “le sigh”

  21. mike April 19, 2013 at 9:37 am #

    And what if the situation is reversed? I am 28 and have never had a girlfriend, never had sex and had one, first and only, kiss in my life… Will you, as girls experienced in relationships, want a relationship with me and think of me as an undiscovered gem or be totally scared off by this fact and consider me someone with whom something must be dreadfully wrong, because no girl before loved me? And those of you who have never had a boyfriend, would it be attractive then to have the first relationship experience with me? Any of you, guys, had a similar story to mine? Any insight you could give me on this would be very valuable.

  22. renee April 19, 2013 at 9:49 am #

    well.. i find it hard to answer your questions. i think that essentially, when you find the right person, your thoughts and queries above are irrelevant :). it depends on the person you are and the chemistry that’s held between say, you and i. if i was attracted to you and all seemed to work out well, then the fact that you’d kissed one person and not had sex before would be interesting at the very least (in a good way :)… but really, not important.

    each to their own and that’s just my opinion.

    you’d be a gem, as are we all

  23. Lola April 22, 2013 at 3:46 pm #

    I think you’d be a gem as we all are. You sound refreshing compared to the lot of guys I’ve been scoping out. I’m 26 and single and have never had a boyfriend and I’ve never had sex. I find that guys who have been around the block a couple times expect a lot more physical intimacy from me very early on than I’m comfortable with. So I would prefer to date someone who isn’t going to pressure me. This would probably be a guy who isn’t so “experienced” because he would have different expectations, more similar to mine in terms of how quickly the relationship moves and through which path.
    I have a tendency to be drawn to the player type. I’m sure it has to do with growing up in an abusive household and being sexually assaulted. I truly hope I can change my wiring and be attracted to a “good” guy who will treat me right and have enough courage to trust him.

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