“I’m Afraid to be Alone. Should I Settle?”

I met a guy a couple of months ago online. It started innocently enough, but eventually we developed feelings for each other. I gathered some courage and met him in person. He is extremely good-looking, in addition to being caring, loving, and insanely sweet. He also genuinely loves me.

We decided to start a relationship. We knew it was going to be hard (we do not live close), but we gave it a go. However, there are a couple of issues. He is a struggling musician who is a server in a restaurant. He got a DUI about a year ago, and he was forced to quit his job as a personal trainer. He is living with his grandparents, and even though he says he will move out when he can drive again, part of me believes that won’t happen. He tells me that his music career will pick up after he is able to drive, but I realize it is extremely hard.

At this point, I would like to point out that I’m an Ivy League student, and I got a really good internship as a banker in New York. I like to have deep conversations about the nature of current events and finance — something I have never been able to share with him. We do share interests in music and art, but that is about it.

I also worry about his future. The music industry is really hard to make it in, and I have let him know this but he says he will try harder and if worse comes to worst, he will go back to personal training. Also a big red flag for me is that he is not a college graduate. All this breaks my heart because I genuinely love him, but I don’t know if our futures will unite. I have thought about breaking up with him.

Now get ready for another issue. I am afraid of breaking up with him because I don’t want to hurt his feelings (it would kill me if I hurt him) and because I am afraid no one will love me as much as he does. He adores me. He wants a future with me. I am about to graduate college and I am terrified (scratch that, petrified) of the dating world, especially in New York.

I see it already in my school. Men are not interested in relationships (my last boyfriend broke up with me because he wasn’t ready for a committed relationship, and he didn’t feel it was fair for me), and they just want to date and hook up with girls to eternity. I am also aware that the men who want to commit are older, but I don’t want to date men in their late 20s or older. Men also outnumber women, etc. (I have a million random factoids about why it sucks to date in New York). I don’t want to aimlessly date for years, just to end up back at square one.

I already have a boyfriend who loves me. But at the same time, I want to find someone who I can intellectually bond with and find a realistic future with. Sometimes I feel that is too much to ask and that I am being overtly choosy (I already have a really good boyfriend). Should I really break up with my real boyfriend, for an idea that does not exist? Please, I really need some advice. I’m under tons of stress. — Scared to Leave

OK, let’s review: you’ve known this guy all of “a couple of months,” you live far apart, you don’t have that much in common, you aren’t able to have the kind of discussions with him that you’d like to be having, you don’t think he’s an intellectual match for you, AND you don’t really have much faith in him to achieve success in his career of choice, and yet – and YET — you are still entertaining the notion of carrying on some sort of relationship with the guy?

What I find most baffling about this is that you say you can’t stand the idea of hurting your boyfriend and yet that’s exactly what you’re doing by keeping him with a girlfriend who doesn’t really want to be with him but is too scared to be alone. You’re keeping him from potentially meeting a woman who does want to be with him — like, really, truly be with him. Worse than that, you’re keeping him with a woman whose appreciation of him is based mostly on his availability and interest in her, and not so much in who he is as a person. Imagine what it would begin to feel like being with someone who felt that way about you. Eventually you’d figure it out, or at least suspect it, but not before being hurt enough times to finally consider the option that you were merely “good enough.”

Don’t do that to him. If you can’t have faith in your boyfriend, have more faith in yourself that you’ll be OK without him. Have enough faith in yourself that even if you don’t have a longterm, committed relationship by the time you think you’re supposed to have one that you’ll be fine. Have enough faith in yourself that, even if you don’t find the perfect guy right away, there are experiences to enjoy in being a single woman in the city. Have faith that you are interesting enough and smart enough and have enough to offer that you’ll not only attract quality men into your life, but you’ll also attract a circle of friends to keep you company and help enrich your life.

Staying with this guy would be a mistake and will only cause you and him more heartache than you’d have if you just ended it now. You’ve only known each other a couple of months (and long distance, at that). There isn’t so much attachment and history there that either of you won’t bounce back right away. Just MOA and save yourself the drama.

If you have a relationship/dating question I can help answer, send me your letters at wendy@dearwendy.com and follow me on Facebook.


  1. Avatar photo Addie Pray says:

    LW, you are about to start life as a banker, surrounded by lots and lots of male bankers, who will probably share your passion for intellectual conversations about banking! I bet you will fall in love with one of those bankers, have baby bankers, and live happily ever after! You’re too young to settle. … Just don’t wait until you’re 31 when “THERE’S NOBODY LEFT… THERE’S NOBODY LEFT!” (I loved that video from yesterday.)

    1. I just pictured a bunch of little baby bankers wandering around in little suits. That definitely made my morning brighter.

      1. I had the same mental image! 🙂

      2. Avatar photo Addie Pray says:

        Baby Alex P. Keatons everywhere!

    2. I agree wholeheartedly with you Addie Pray. Most people assume that banking is just about the numbers, but as someone who has worked in the field for years with numerous friends and family in the industry, I can tell you my favorite aspect of the work: it is all about the relationships you build with people, your clients, and co-workers especially.

      LW, when you limit the age range you will date to such a narrow field, it makes you sound immature. Maybe you are immature, I don’t know you. Do not be so quick to limit your options in life! Your life will come together in the most unexpected way. I personally am thankful that I had the opportunity to go out on dates with many different types of men; it helped me get a better sense of who I am, what I wanted, and my needs.

      I am dating a man who is the youngest I have dated in a few years at 30 years of age (I am 26 years old), he is also divorced, and has a 3 year old child. A few months ago I probably would have excluded him from the pool of potential dates based on his divorcing a woman so young and his child. These experiences helped mature and shape him in a way that makes him a much better partner. He surprised me and I could be happier that I met him.

      I understand why you might think no dating goes on in the world now. Many of the worst decisions I have made in life were those where I allowed fear to cloud my better judgment. There seems to be a strong hookup culture present today but I can guarantee you that there are men around you who still date women,who will be able to love, respect, and care for you.

      What if you tried volunteering? That way you can gain some perspective on life, be around good people, and make some new friends. Embrace and seek out new experiences of all sorts! You will gain stories and friendships along the way. Good luck to you!

  2. MOA, like Wendy said, because obviously you have more requirements for a boyfriend than “He adores me”, for example, intellectual conversations. Why settle for something that won’t make you happy in the long term?

    You won’t be alone forever, and even if you don’t settle down at 23, or whatever, it’s not the end of the world and you can have some great relationships before you find “the one”.

    And, personally, I don’t see what the issue is with dating guys in their late 20’s-30’s because chances are they have an established career, residence, etc. If you’re looking to settle down, that’s where you should be looking…but maybe you don’t really want to settle down quite so soon.

    Finally, how can men out-numbering women in a city be a bad thing? That means you have more corn in the crop! It’ll be a great harvest this year!

    1. Avatar photo Will.i.am says:

      That’s a problem I face diamore as well. I’m an older guy, 28, looking for someone like the LW. Whether she’s my age, a little bit older, or even younger. The younger girls no longer have the interest to date older guys like they did 7-10 years ago. A couple years out of high school, I knew a few women who married men 10 years their senior, and now I haven’t found a girl comfortable dating a guy just 3-5 years her senior. What’s funny about the LW is that what she is looking for, will most likely be found in an older guy. Statistically younger men don’t really start growing up till 25 or later. What she really wants is an older man, but is scared by his age.

      For the LW advice, I would just move on from this guy. You don’t want to wait for him to attain his goals and you don’t have too. If you don’t like him as the way he is now, I doubt you will ever like him. Even if he does obtain some of the goals you want, he will eventually find something that you don’t care for at all. Like the stupid saying I see on Facebook all the time, “If he doesn’t like you at your worst, he doesn’t deserve to see you at your best.” It’s cheesy, but it’s actually a little bit true.

      1. Avatar photo Addie Pray says:

        Hey, LW, I want to introduce you to my friend Will. …

      2. Avatar photo Will.i.am says:

        Ha. Thanks AP. I need all the help I can get!!

      3. Will, why are you interested in younger women? Just curious.

      4. Avatar photo Will.i.am says:

        It’s not interested, it’s just due to my area, they have more of what I’m looking for. My area is known for marrying young, having kids, and then getting divorced. So a single parent ranks low on my list of what I want. Post 25, most women are single parents here or happily married. So, I’m kind of stuck being the “creepy old man.” Don’t get me wrong, I would love a single parent that had her shit together, but a lot of them are like what the LW wrote in about. They have goals but aren’t really putting one foot in front of the other to make them happen, so I’d end up “wasting” a good amount of time waiting on them.

        My area is full of single educated men, but not enough equal women to go around…..

      5. Where do you live?????

      6. Avatar photo Will.i.am says:

        Fort Smith, AR (Arkansas not Arizona)

        It’s about 57 miles south of Fayetteville, AR which is where our State University is located.

      7. Not the same Amy that commented before above lol.

        I’ve always had trouble trying to date guys my age because I have lived a tough life and was financially on my own by the time I was twenty. Everyone else that I knew wasn’t like that so I looked for older guys, even if it was just a few years. That didn’t make them any more mature though lol.

        I get what you’re saying, Will.iam, it’s not that you have anything against the girls in your area, they’re just not your type. It has to do with life style and maturity.

      8. Avatar photo Will.i.am says:

        Correct. I still casually date, since I find most of my dates online, so it’s already a numbers game. Most of my friends that are committed spend a lot of time with other couples that are committed. So it’s hard to find that single girl that is looking for the same things you are, and have enough attraction to each other. I’m not saying I want to marry a week after meeting, but I’m much more focused on the overall picture. I hope to wed only once, so I’m looking for that complete package that makes not only her happy, but me happy too.

        It kind of works like this. A cute, college educated girl could end her relationship right now and probably be asked to go on a date by this evening. My area is so full of single men, that women who are attractive and educated have no problems. Too bad these women aren’t always attracted to me. Interaccial is not the happening thing in my area, which also makes things a bit harder as well.

      9. My area suffers from male over-saturation too. Typically people come back in their late 20’s/early 30’s to raise their families here so not many college-educated women in their mid-20’s make their way back this way…most of the women that stuck around are dating d-bags that never left home either so college degree isn’t necessarily a requirement for me, haha.

        And I don’t mean to imply that never leaving home = d-bag it just seems that most of the women I would be interested in are dating “brah-bags”.

      10. Avatar photo Will.i.am says:

        It’s no biggie Budj. I never left home, because I love the area. I also made something for myself in the area. I would LOVE to raise a family here, but I know my area has tremendous shortcomings if you want to date. It’s perfect for a family, but is sorry for the typical dater.

      11. Avatar photo Will.i.am says:

        I’ve explored options of dating single parents too. I don’t want anyone to think I shun them, it’s just most of them have a baby daddy that’s not too involved, so a lot of financial pressure is upon them. They truly live the life of “can’t see the forest for the trees.” Also doesn’t help if they can’t get help from family or friends to go back to school, so they kind of end up getting stuck in a cycle. I’m so glad I was fat and shy into my early 20’s. Who knows where I would have ended up!

      12. Wow, apparently I need to move there. I’m 28, never married, no kids, no STD’s and have a bachelor’s degree. And I have mad skills in both the kitchen and the bedroom.

      13. Avatar photo Will.i.am says:

        Ha. Much cheaper than CA. AR is the 2nd cheapest state to live.

      14. CA is a great dream but every time I run the numbers, I’m too poor to even get out there. For now, I’m staying put and socking away as much overtime money as I can in my savings. Hoping to be able to move somewhere by the end of the year.

      15. Avatar photo Will.i.am says:

        That’s what you should do. Moving is a horrible idea. Get your feet under you first and then decide if you even want to move at all. Most likely, once you get your finances in order, you may like where you live more.

      16. Can I ask you Will – is there a reason you choose to date outside of your race? I understand being open to different backgrounds or race being low on the list of what someone considers and I understand the people for whom race/culture is a huge factor and will only date inside their races but I never quite have understood when race is a primary factor for people who don’t date what they themselves are. Of course you don’t have to answer but I’ve always been curious whenever I come across this so any insight you can offer would be appreciated. tx.

      17. Avatar photo Will.i.am says:

        No problem at all. There’s not a lot of black women in my area that aren’t into dating schools. I grew up going to schools that were predominantly white, and I grew up on the “white” side of town my entire life. So being around that all the time, since I was 5, it kind of sparked my interest as well.

        Many of the black guys I know that grew up on the “white” side of town, also have an attraction to white, asian, or hispanic women. I love black women as well, but they are more into the thug men. I’m very far from thug.

      18. Avatar photo Will.i.am says:

        Ugh. Schools should be thugs. I will add that white women date thugs too, and I’m not interested in them either. Not a race thing, but lifestyle choice.

      19. Thanks – makes good sense to avoid anyone interested in thuggery.

      20. Moneypenny says:

        Apparently I maybe need to move as well… There are a whole lot of women and gay guys where I live, which doesn’t help my chances…

      21. I think we should start a exchange. Women who are ready and want to settle down in nice family friendly areas can move South. Men who want a gf and experience all that city life has to offer, can move to the Best Coast 😉 Hey it worked for taming the old wild west amirite?!

      22. Avatar photo Addie Pray says:

        amy (not to be confused with Amy): I want to introduce you to my friend Will…

      23. rangerchic says:

        Hey Will.i.am, I am in Fayetteville, AR!! Small world 🙂

        Anyway, you should make it up to Fayetteville for the dating scene. I’ve lived near Ft. Smith and my grandparents are there so I travel there regularly and I know exactly what you mean. Fayetteville is a bit better with the college and all. I wish I had/knew some single women – I would totally set you up!!! 🙂

      24. Avatar photo Will.i.am says:

        I’ve been to Fayetteville many times. I had a buddy that lived up there for 3 or 4 years. Sadly, he moved to Fayetteville, NC. I don’t have the connections that I once had, so I usally end up there in passing.

        Knowing single women is definitely the round peg trying to fit in a square hole. I do know one girl who is married to a ranger. To keep your identity secret, are your maiden initials KC and your husbands first initial M?

      25. I am sorry to have to say this, and hope nobody calls me a spoilsport! And I do enjoy these side conversations, but… maybe this thread should move to some kind of a forum thread?

      26. Avatar photo iwannatalktosampson says:

        NO!!! These side conversations are my favorite – and sometimes the forums die quickly I think because people forget about them it they didn’t have one of the 5 most recent comments. If I ever write in everyone has my permission to side converse.

      27. Avatar photo Addie Pray says:

        I adore side conversations too and I particularly like them when they involve getting dates for our DW men. So, no, do not take this to a forum. Period. (Addie Pray has spoken.)

      28. rangerchic says:

        Well, I know you might not get this as I am replying late but that is not me! I picked that name from a favorite book character. Though it would be cool if my husband were a ranger 🙂

      29. Yeah, I know, my boyfriend is 7 years older than me and I have friends dating men 15-20 years older, and we’re in our early 20’s. I think it’s a lot easier, especially when you’re more mature, to date people older than you. Then again, I’ve always got along better with people far older than me.

        I think when girls who are looking to settle down should be looking for a well-established mate because they can offer opportunity, like children, marriage, etc. Younger guys don’t necessarily make the cut.

  3. Honey… you NEED to be ok with being on your own. This is coming from someone that has been in a few bad relationships because at least I was with someone that I knew couldn’t hurt me because I already knew that they didn’t like me. Messed up? Yes. Did I go to counseling and get help? Absolutely, now I am in a healthy, happy relationship with my fiance’ who is in Colorado while I am in New York. We are both working on our masters degrees and I would begin to panic about being alone with him being gone. I was not alone, I had friends, family, etc. and I could talk to him. You are not alone, even if you leave this guy.

    I also wanted to talk about the music industry. There is no “making it big” anymore. My fiance’ dropped out of college (long before we met, he must have been 20ish at the time, he just turned 30) to tour with his band. The ONLY reason why they were able to tour around the country and open for bands like Jimmy Eat world etc. is because someone found them on ACCIDENT. One of the band members was doing construction on a house that just so happened to be a house owned by someone in the music industry. The band member was playing their music and that’s how it all started.

    They toured for a few years, the band broke up, my fiance’ came home after a few years, devastated. It took him years to get his life back on track. He DID open a recording studio but even that was not enough to earn a full time income. He LOVES recording bands, but right now, he’s back in school to become a college professor because he knows that music is not the way to earn a full time living.

    I am incredibly happy that I met him at this point in his life. Also, if you do stay with your guy and if for some reason he DOES make it big, he will be gone. A lot. And you will be alone.

    Be OK with being alone. Be ok with leaving a relationship in which you are NOT in love. You should be with someone that you LOVE. And he should be with someone that loves him too.

    MOA and get some counseling to be ok on your own.

  4. I think I´ve said it on here somewhere before… in spanish there´s a saying that roughly translate to “Better alone than with the wrong companion”(Mejor sola que mal acompañada) and I truly believe that.
    I´ll never understand why so many people (esp. women, lets face it) are so afraid to be “alone”. Would you rather tie yourself to this guy and miss out on the chance for the right guy when he comes along???

    1. I said to a counselor once “I just don’t get it… I feel more alone with so and so than I felt what I was single”. You just feel more lonely when you’re with someone that doesn’t make you happy. It’s tough and scary to be alone but it’s something that needs to be faced rather than settling into unhealthy relationships. If you’re not ok being alone with yourself, then you won’t be ok in relationships.

      I suggest to get a pet lol. You don’t have to be a crazy cat lady or whatever, but there is something sweet about coming home to a cat that is ecstatic to have you be at home.

    2. I’m with you..I see friends in relationships that clearly don’t work but still they stay. I don’t get it.

      1. Yeah, I donpt know whatps worse, the ones that stay with guys that are clearly wrong for them or the ones that are so desperate to be with someone that they last like a week single between BFs (who of course is also wrong for them).

  5. evanscr05 says:

    You like what you like, and if he isn’t enough for you, why waste your (and his) time? You can’t stay with someone you don’t love (and, for the record, what you feel for him is most definitely NOT love) just so you don’t hurt their feelings. His feelings will get hurt one way or another by being with someone who doesn’t want to be with him. Plenty of people get broken up with all the time for reasons that don’t go beyond incompatibility – doesn’t mean there is anything wrong with him, or your relationship overall, just that the of you are not a good match long term, and that is perfectly fine. Put your big girl panties on and do the hard thing and break up with him. He deserves someone who cares for ALL of him. And you need to be alone. Graduate, get a job, and enjoy all that single life can bring, especially in a city. You’re clearly not ready for a long-term relationship yet, or at the very least, not one with this particular man.

  6. LW, You could use a good bit of reframing and attitude adjustment as you seem to be stuck in a place of negativity. Let’s review the facts here:
    1. You’re about to graduate from an Ivy League school (congrats)
    2. Your degree, elite school status, and location in NYC will probably translate into at least a decent, but more likely, a high paying job within a few years.
    3. You live in one of the most populated cities in the US
    4. You’re still [presumably] in your lower 20’s.
    5. You say men outnumber women. Well I don’t have any statistics to know if that’s true or not, but let’s say it is for the sake of argument. That’s a GOOD thing for you as it would give you more options.
    6. You are not intellectually engaged with your BF.
    7. You worry about his financial earning potential down the road.

    1-5 prove that you have a lot going for you in terms of dating odds and as a good catch. There are tons of single men in NYC that want a girlfriend. To believe otherwise is silly. Will you meet a lot of guys that still just want to play the field, yes. But you’d meet them where ever you live. It just seems like a lot of them because NYC has more population. Take a moment and reflect on the types of men you’re getting attracted to and see if there’s some sort of correlation as to why you’re running up against many that say they don’t want a relationship. And by the way, often times when guys say that it’s just a nicer way of saying they’ve decided they don’t want to be in a relationship with you. OH and another thing, you say you can’t find guys that want a relationship, but didn’t you meet one of those a few months ago? Hello! Bet you can do it again. #6 and 7 shows that your relationship is not in a good place and I read it in the way that says you don’t have the confidence that you can have a fulfilling marriage with this guy. If your relationship is doomed it would be better for it to end sooner rather than later. It would make it less painful than waiting and it would return both of you to the dating pool. Only you can decide if you can be with someone that’s not at the same level as you intellectually (but it sounds like you already have). You could try looking at his intellectual abilities in other fields like music and see if that’s satisfying for you, but if it’s not I think that would leave you without any options but the one you fear.

  7. You’re so young, don’t settle now! As a girl in NY, I will fully admit that dating in New York can suck. You’re right, there are guys who don’t want a relationship, they just want to hook up. And many of them do wait until they are older to start thinking about finding a girl to really be with. But that doesn’t mean you will be alone forever. You’re still so young! You have a lot ahead of you and you have a lot to figure out still. These first few years after college are your chance to really do that and staying in a relationship just for the sake of having someone who adores you isn’t going to help you with that.

    The comment that really stood out to me was this one: “I am also aware that the men want to commit when they are older, but I don’t want to date men in their late 20s or older.” It makes me think that you really aren’t level for the type of committed relationship that you think you are ready for. If you’re not willing to go outside your limits, you may not meet the right person. I’m not saying you have to accept every date you are asked on or that you should date someone that is twice your age if it makes you uncomfortable, but you have to be open to possibility if you are really looking for that kind of relationship.

    Good luck.

    1. AndreaMarie says:

      Perfectly said. As a girl whose been in the NYC dating scene since college I can attest that Yes most guys here wait until they are alittle older to settle down. NYC is a career driven town. Men want to climb the corporate ranks alittle and get some financial stability and money in the bank before getting serious.

  8. I don’t even have to read the letter to know the answer-no. Never settle.

    In my opinion, I’d personally rather sleep alone the rest of my life than be in a relationship that didn’t fulfill me. You don’t do yourself or the other person any favors. I can promise you this. That sounds definitive, and I know it is, but this is something I feel pretty strongly about.

  9. With everything you say, he doesn’t match up for what you want. So don’t keep stringing him along. And even though you say he is a great boyfriend, he doesn’t sound that great with all of the red flags you mentioned (I mean, to me a DUI is a deal-breaker). You spend most of the letter talking about the minute details in how he is not right for you. And that’s okay. But you have to tell him, and more importantly, tell yourself that he is not right for you.

    You have met this guy at least once in person, and you say you love him, but you love the idea of him and a relationship because you’re so terrified of being alone. And yeah, learning to be alone is hard, but you have to do it. I went through relationships one after another without ever being alone, and when I finally was alone for awhile, it sucked. But, it taught me what I really needed and wanted in a relationship. And it taught to me to value all of those things that are important to me and not settle for anything less, because I won’t be happy otherwise. And your happiness is ultimately more important than settling for someone that isn’t right for you.

    Don’t base your happiness on someone else. And no matter what, even if you are deeply in love with someone, you never know if something tragic will take their life, causing you to be alone. Finding love is not the end-goal in life.

    Having lived in NYC, I know what you are talking about when you say you don’t like the dating world there, but honestly, it’s not that bad after awhile.

    Just remember, you may want a boyfriend, but you are not going to be happy with a boyfriend who doesn’t fulfill your wants & needs in a relationship.

    1. Moneypenny says:

      Exactly, good point in saying, “don’t base your happiness on someone else.” You are setting yourself up for disappointment! I believe that it’s the most empowering to be in control of your own happiness and destiny, and choose to surround yourself with things that will bring happiness to you, like, a great job, good friends, hobbies, etc. that will make your life shine. Like the saying goes, “happiness comes from within”- it’s totally true.

  10. sarolabelle says:

    Some people really don’t know what love feels like when you do feel it….LW, you don’t love this guy!

  11. This letter is a good example of why men that age are ‘afraid’ to commit. He’s nothing but a proxy to her, for her status and lifestyle aspirations.

    1. SweetsAndBeats says:

      I’m sorry but I’m pretty sure that part of the reason this man is so in love with her is because he knows that with no formal education and champagne tastes, he’s going to need a sugar mama. The LW is not some wicked witch, she’s just uncertain, and I don’t think the man should be pitied in this situation.

      1. I’m pretty sure I wouldn’t put all my eggs in one basket with a college student if I was looking for a sugar mama. And I wouldn’t accuse him of that at this point either….seems more like he thinks he is going to be a rich and famous rockstar at this point.

      2. Dude speaking says:

        She is the one talking about money and his apparent lack of it. Yet he is the gold-digger?

        Also, you overestimate her chances of being a successful investment banker 10 years from now. She will likely (I mean that–likely, as in over 50%) not be in that career when she is 28-30. It is more likely that she will be in a far less demanding and less lucrative position, making her upper middle class money and working 50-60 a week for that.

        I am not saying stay with him—it sounds like she already moved on, but just doesn’t want to let go for keepsies until she has another man set up–but she should not assume she will be the fount of cash you seem to think.

      3. Where did the Champagne tastes, and absence of formal education come from? You make him sound like Tarzan the Gigolo. Long range planning does not seem to be this guy’s strong suit. So I doubt that he’s got some elaborate plan to hook his wagon to a bank intern.

      4. Well she is not very kind to her boyfriend. I have sympathy for him.

  12. its sad to think that someone who is probably my age is so terrified of being alone. i cant IMAGINE “settling down” now (getting married, having babies, ect) .im too young. way too young. LW, think what you want out of your life. what YOU want. do you want a successful career? do you want to travel the world? do you want to have a dog? ect, ect… do that. if you find a person who wants to share those experiences with you, thats great. but live your life, dont just conform to some insecurity in yourself or to some “formula” that society has put on you.

    there has to be some serious shift in the way we raise our daughters if so many women in this world are so terrified to be alone that they will just take any guy who likes them.

    1. Loved this.
      And I´ll try to do my part in raising my 2 girls 🙂

  13. GertietheDino says:

    Move on sweetie, people get hurt, sometimes we are the ones doing the hurting, but we all live through it. He will and you will too.

  14. I couldn’t help but be bothered by the entirety of that 3rd paragraph….ew.

    Anyways…I will chalk this up to you just not being that into that guy and have faith you may judge someone differently when you aren’t using them to prevent being alone and actually love them for them.

    1. Avatar photo Guy Friday says:

      I couldn’t help but be bothered by the entirety of that 3rd paragraph….ew.

      THIS. I’m so glad someone else said that, because, sorry, but that came off as SUPER snobbish to me, and in the context of the letter it made me feel like a big part of your issue here was — and I’m sorry if this comes across as harsh, but I feel it needs to be said — you’re a college student in a college student’s world of deep philosophical conversations about everything, and you feel like you’re on this gold-lit road to success that you can’t possibly be knocked off of, and how dare you have an anchor like this guy who has no college degree and doesn’t talk to you about the NASDAQ index or the fluctuation of the dollar’s power against the yen?

      Look, you don’t want to be with the guy for a number of reasons. You don’t feel it, and he doesn’t fulfill what you’re looking for right now (though I’d note that it certainly sounds like you’re assuming he’s not capable of “intellectual” discussions because of his career path, not because you’ve actually tried to talk about more than financial things.) So move on for both of your sakes, and it’s always better to do it for everyone involved as soon as you realize there’s no forward progression in the relationship. But, for what it’s worth, a piece of advice for you: the real world isn’t like college, and if your internship turns into a full-time position — and with the current economy, it’s by no means a guarantee — you’re going to be working so many ridiculous hours that the only way you’ll survive in the world is if you find someone or something that is so decidedly NOT of that world that you can go to him/her/it when you need some grounding and normalcy. I married my wife for a multitude of reasons, but I won’t deny that one of them is that she’s not a lawyer and couldn’t possibly care less about the hot new Supreme Court decisions and what they mean for my clients. We have plenty of intellectual conversations; they just don’t deal with the law. And if I had married someone who wanted to talk about my job non-stop, I think I’d probably go insane, because I need that separation from work that my wife provides. Just food for thought.

      1. Nice.

      2. 6napkinburger says:

        Not exactly. That was one of the only valid points I thought she had. I dated someone who I couldn’t connect with intellectually and talking about things that interested me or current events or “important issues in the world” made me so frustrated that I wound up mad at him for not getting it and he’d get defensive because he didn’t know why I was mad and I could tell him and it was horrible. Which eventually led to our breakup. So I think that that is INCREDIBLY important and there is almost no way to talk about it without sounding snobby.

        Though the rest of the letter made me nausiated. Seriously, was she serious with this? She’s 22, she is asking if she should “settle” for a loser she doesn’t like because dating in New York is hard? If she went to an Ivy league school, then she isn’t only hanging around people who get married when they’re 22. (Basically) None of her friends are getting married, only a few of them will stay with their boyfrineds longer than a couple months out of college, and she is being an overly-dramatic moron. But not on that one point.

      3. Moneypenny says:

        Yeah, nice! Well said.

    2. Yeah it was a bit snobby, but I was the same at 22. very proud of all that learnin’ and wisdom I’d gained at college. I think she mentioned it because she’s worried that this could be a big problem down the road. I don’t think it will be.

      1. It won’t be if she can get over it. I think she has already kind of skewed her perception on this relationship though. Hopefully the next one is better.

  15. I didn’t even need to read your letter to know the answer to this one… No, you shouldn’t settle. It’s not fair to him, and in the long run it won’t be fair for you either.

    I feel bad for the poor guy who you’re clearly using so you don’t have to deal with your emotions.

  16. LW, I feel really bad for your boyfriend. You doubt he’ll ever move out of his grandparents’ house. You doubt he’ll be successful in his career. You are skeptical that he didn’t get a college degree. Honestly, it sounds like you never even gave this guy a chance.

    In this situation, yes, you need to MOA. You’ve already made up your mind about this guy. It’s time for you to be single so you can work on yourself. You’re young and have time on your side. Next time you date someone, however, please go into the relationship with an open mind. Even if it doesn’t seem like he’s the EXACT guy you’re looking for, take a chance. It might surprise you.

    1. That was my reaction. If he ever finds out what she thinks of him, she won’t have to worry about breaking up with him – he’ll dump her.

      This is why I always cringe when women talk of ‘settling’. Because this discussion inevitably reveals some very ugly attitudes. Realistically no one is ‘settling’ for anyone. There is no hierarchy running from mercenary banking interns down to personal trainers. No one ‘deserves’ to be with someone of a given status. It’s just a narcissistic fantasy. People who think that way deserve to be alone.

      1. I really like how you put that, Leroy. It bothers me when people have a list of qualities for their “perfect” match. In reality, that drastically narrows the field of guys/gals to date. Say I was looking for a boyfriend…I decide that I ONLY want one with brown hair, blue eyes, 6’2″, age 23-25, is a dog owner, makes at least $60,000 per year salary, and drives a Honda…I’m narrowing my dating field considerably. That’s my impression of this situation.

  17. Sunshine Brite says:

    No don’t settle. I could tell that even before you went through the umpteenth number of reasons why you don’t work together. I’ve heard most everywhere has some of those same challenges as you gave for NYC to be less than ideal for dating yet people tend to meet up in all areas. Sometimes it’s with the last person you thought would be right, but they’re right for you. Keep your standards high, figure out your dealbreakers, and go for it.

  18. If you want a certain type of partner – then look for that type. Killing time with someone you feel is not for you wastes your time and is cruel to him. Free your boyfriend to find a woman who appreciates him and doesn’t feel she is settling to be with him. Go be single. It is not a bad thing – date lots of men – figure out exactly what you want and find that in your next boyfriend. Men aren’t placeholders in our lives, a boyfriend shouldn’t be a box you check-mark once you have found a warm body for the role.

    1. Hey FireStar, I’m meeting the Guyanese half of the family today. Under shitty circumstances of course… do you think they’ll be much different than the Trini side?

      1. Hey MissDre – In reality we are actually quite similar – which is why we are so vocal about how we are nothing alike! I hope your sister-in-law gets better soon.

      2. Thank you very much. We are all really praying hard. The neurologist said he is hoping to see her become a bit more responsive by the weekend. Every day I pray it will be the day she wakes up.

  19. If you know this guy can’t make you happy, then you should MOA for your sake and his. I can understand wanting to be with someone with whom you can share intellectual conversation. That’s important to me too. It did strike me as a little odd that you would think twice about dating a guy who isn’t a college graduate though. To me, what’s on the inside is way more important than any piece of paper they ever earned. My ex only had a GED while I have a bachelor’s and that never bothered me a bit. He was also one of the smartest guys I ever met, just too defiant to conform to rules like doing homework. So I guess the great intellectual conversations we had were enough and he didn’t need a college degree to win my love.

  20. AnotherWendy says:

    Big life lesson: just because you love and care for someone it doesn’t mean you have any business being in a romantic relationship with the person. This is a perfect example. Let him go.

  21. Stanfishing says:

    Wow…I know so many women just like the LW. I admire the conquer the world attitude and I dislike the take no prisoner approach. You’re doing whatever it takes to fulfill your emotional needs temporarily until you “make it after all” (look it up). Throw your hat high into the air and do a spin for us all when you finally get there. Just please do it without this seemingly good yet uneducated man who just may have been your soul mate. Honestly, you have allot going for you but from a man’s perspective…I would imagine most would take a pass, they just don’t care. This guy will also take a pass, just let him figure out what’s truly going on. Just like the women or guy that puts their mate through school and then gets left behind after that person finally graduates. The only difference is your currency is just love, and your account is being drained. I shiver to think of how he would feel if he was also helping you pay for that fancy degree. But hey, you may find him temporarily more attractive.

    Please let this guy go. I just know he brags about you to and the thought of that is…well…sickening, sorry!

    BTW I am VP of a company and have hired one person from and Ivy league school in my life. Let’s just say I hope your new job is filled with the same type of individuals as you. To be blunt, us normal non-ivy leaguers don’t care about where you went to school beyond the interview and light conversation. Just being honest here. Everyone’s been around that person who went to Harvard, or has their masters or whatever advanced degree and will not let you forget it. Don’t forget the license plates to your new B-mer when the time comes, “eye m n iv.”

  22. LW, this is the line that stuck with me: “because I am afraid no one will love me as much as he does…” I *really* hope that this doesn’t sound patronizing, and I apologize if it does… but here goes:

    1) You’re 22! You have your whole life ahead of you to meet someone and be loved, and adored! Yes, dating in NYC is difficult – but not impossible. Yes, guys who are in their early 20s want to screw around for as long as they possibly can. Yes, male investment bankers can be arrogant &#@#heads (full disclosure: I dated my fair share of them, and as a management consultant am trained to not like bankers). But, also, why the huge rush to settle down now? I too thought when I was 22 that I was ready for marriage, etc. I would have said yes if my (investment banker) boyfriend at the time had asked. That would have been one of the biggest mistakes of my life. 4 years later, I would have said yes to the next long term relationship. Would have also been a huge mistake. You’re going to learn and grow so much through this job, living in NY, and being outside of school — don’t for a second imagine that who you are now is set… you;re going to be even more amazing in 5 years than you are now – and there are so many men out there who are worthy of you, and (more importantly) what YOU are looking for…

    2) for the harsher part… I don’t think this guy loves you. He may be infatuated with you. He may treat you well. He may adore you. He may really *really* care about you. He may be loving… But he’s young, lives far away, and is still dealing with his own life. I also don’t think he loves you because I don’t think YOU love HIM (in the life-partner sense, anyway). You haven’t accepted him for who he is, without hoping that he’ll change, and see someone who is all you need even in spite of deficiencies. Love is being able to say that you can intimately catalogue someone’s major flaws, and ACCEPT those without ever thinking that this person isn’t good enough for you. If you ever wonder if someone is good enough for you then there isn’t love there… And while you might not have stated it explicitly, your mentioning that you’re at an Ivy with a banking internship in NY means that you’re placing yourself “above” him. Let him go. Grow up (not in the patronizing sense, just in the “we all have to do it” sense). Find someone who you think is everything you need in spite of their imperfections. THAT is when you’ll find love.

  23. PS — my boyfriend and I both went to top 15 universities for both our undergrad and master’s (MBA, JD). He’s a lawyer. I’m a consultant. We both pretty much get paid for our brains. The amount of times we’ve had an “intellectual” conversation in the 4 years we’ve been together? Rarely. My best friends husband never went to college. He’s a musician. The number of times I’ve had an intellectual conversation with him? Countless. Get out in the real world and recognize that your education doesn’t actually mean what you think it means.

  24. It sounds like this LW was asking for a pep talk to dump her bf, which Wendy appropriately gave. You should not be in a relationship based on a fear of being alone, it isn’t fair to anyone involved.

    I’d caution you LW, however, that as you get older, you may place less value on traits like an obey league education or the ability to talk finance. I think that as you mature, you find that there is a lot more to genuine long term relationship compatibility than having every superficial trait in common.

    1. Obey = ivy, stupid phone

  25. Avatar photo bittergaymark says:

    WTF? Good lord! Now this letter seems fake. Ironic. The one guy on here who is constantly accused of misogyny on here and even I can’t believe that any Ivy League educated women could be this vapid, this silly…or any of the other myriad of S words that immediately spring to mind…

    PS: NEWSFLASH. Nobody genuinely loves anybody after a couple of months. Especially when they don’t even live in the same town… And there is something latently narcissistic about believing that oneself is so wonderful that to break up with anybody would truly devastate that other person’s life beyond repair… MOA. Trust me. He’ll survive. He’s a waiter. He’s a musician. He’s kind of a loser… (Yay! Nothing’s sexier than having both a DUI and living at home with one’s grandparents!) But hey, he’s obviously HOT, more than that, he’s a HOT MESS!! Which means (of course!) he’s probably already beating off vast amounts of women with a stick, it seems.

    1. SweetsAndBeats says:

      Honestly, he sounds like an ‘Ashton Kutcher in Spread’ in the making.

  26. Wow! Let the guy go. This struck a major chord with me: “(my last boyfriend broke up with me because he wasn’t ready for a committed relationship, and he didn’t feel it was fair for me)….” Your last boyfriend is WAY more mature than you are, in that he was HONEST with you. You’re not being honest with your current boyfriend, nor with yourself. And to be honest with you–you’re selfish!

    You don’t seem to want to settle with your career, so why would you settle with this relationship? What happens when you do meet someone who piques your interest in all the areas you require; are you still going to keep the current boyfriend because he “loves you”? You need to get comfortable with yourself first by being ALONE before you can offer to be comfortable as an appropriate partner with someone else.

  27. Don’t do this to him. Don’t settle for someone you don’t really love just because you don’t want to be alone. Make friends. Volunteer. Adopt a shelter pet. Focus on your burgeoning career. Do anything but settle for someone you don’t really love.

    You know what’s lonelier than being alone? Being the person someone picks because they don’t want to be alone. You said you don’t want to hurt him. This would hurt him beyond measure. Do you want to be the type of person that inflicts this sort of hurt on someone? Do you want to be that selfish? I don’t think so.

    Get some therapy and work on yourself because you sound like you’ve got some self image issues you need to resolve. Please get to a counselor to get past your fears of being alone and dating in NYC, which I think is a cop out. Dating is tough EVERYWHERE. Guys wanting to hook up aren’t exclusive to the five boroughs. There’s no ordinance on the books keeping men who want to commit out of greater NYC. I think once you get over your anxiety and fears, you’ll be more likely to find a partner who is right for you.

    Note I didn’t say you WILL find a partner. There’s a chance you may never find the right one. You have to be ready for that possibility, too. That means you have to learn how to love, live with, accept yourself as is. It means you have to accept the fact that “happily ever after” doesn’t necessarily mean “happily partnered ever after,” and that it’s fine to live a solo life.

    First step on this journey of self acceptance is to be comfortable with yourself and unwilling to settle. Let him go. MOA. Good luck.

    1. moonflowers says:

      I wish I could thumb this up a million times.

  28. 6napkinburger says:

    This letter made me vomit a little in my mouth. Sorry.

    1. You should be sorry. That’s a horrible thing to say. FFS.

  29. landygirl says:

    You should absolutely settle, you may never find another man again.

  30. MOA. Here are some points to consider.

    1. He’s never going to make it as a musician.
    2. that doesn’t really matter, since you have lots of earning capacity. He can be a house-husband.
    3. All those bankers you’re about to be mixing it with? They’re going to be after the secretaries and hot chicks at the bar down the road; don’t take comfort in the fact that you’ll be rubbing shoulders with bankers for the rest of your career because it won’t help.
    4. If the sex roles were reversed in this story (ie you’re a guy and he’s a girl) you wouldn’t care about his earning capacity so much as whether he was hot and good in bed.
    5. He loves you. He’s sincere. He’s a dreamer.
    6. “I like to have deep conversations about the nature of current events and finance — something I have never been able to share with him.” I noticed with interest that you didn’t describe him as stupid. Just, not educated. His lack of interest in finance and current events isn’t as important as you think it is.

    However, the big problem in this relationship is that you don’t respect him. You think you’re better than him. Maybe you are! And you’re unsatisfied and feel unfulfilled. And having crunched the numbers and stared into the abyss, the response should not be to settle with your current boyfriend. The rational action for you is to give yourself a time limit and search hard for a husband within the next 24 months, or something like that. Get out there, play hardball, and find Mr Keeper.

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