127 lbs lost, yet still a failure

Have you worked with a therapist at all?

I ask because the degree of your distress and despondency will likely require more than you will able to get out of putting it all out here on a message board.

I wanted to add...I grew up with a guy who was effeminate, over-weight, mama's boy, quiet, Christian. Sweetest guy ever.

He went to medical school and then residency and bought a house. THEN he met his now wife. He was never in a relationship before that either. Same with his brother, married the first girl he was serious about. The doctor was 40 when he met the wife. She was in her twenties. They have two kids. The other brother was attractive, charismatic, took a regular job and was married by 23. They are still together too.

Everyone has a path.

Honor yours.

Firstly, congratulations! You should be proud of your weight loss and all of your other accomplishments, regardless of whether or not they resulted in the success you were hoping for.

I am going to preface this by saying as someone who spent all of her teenage years and early adult years sobbing because she was certain she would never be enough to be loved I get where you are coming from and want so badly for you to find love. And because of that I am going to try to go down every route that I think might be the reason you aren't finding anyone. I have no idea if they apply to you because I don't know you. But I want to try to leave no stone unturned, even if it might be uncomfortable to hear.

Let me start by saying it likely isn't the weight that is keeping women away. I and many other women love a bigger guy. It makes me feel protected, smaller (and what woman doesn't want to feel small?), less self conscious, like I don't have to eat like a bird around you, and bigger guys are just better to cuddle with. I am not saying that you shouldn't continue to try to get healthier, just that it likely isn't the reason you are being turned away. Do you have a trusted friend you could ask for candid advice? Tell them that you want to know what it is that might be turning women away, even if it will hurt your feelings a bit. Ask them specifically to look at your personality and not the weight. If you have a close female friend maybe ask if you could take her on a pseudo-date, act as you would with a regular date and then let her give you tips as to what might be causing women to not be interested. It may be that you are coming on too strong - as much a girls love a commitment, if they can sense it's a wifey audition they might get freaked. There are of course other things you might be doing but I am in no place to speculate about them since I don't know you.

As far as appearance goes maybe you should focus on things other than your weight. Maybe get a new haircut or try different clothes or buy new glasses. Watch Queer Eye on Netflix and try to apply some of the grooming and wardrobe advice. For me it is way more important that a guy have a decent sense of style than how much he weighs. Aim for something that is just a bit out of your comfort zone. If you typically wear camouflage and cargo shorts try a nice plaid shirt and dark jeans. If you typically wear the latter try something a little nicer. Just upgrading these things about your appearance can make you more attractive but MUCH more importantly give you the confidence that women love oh so much.

I also want to echo what other people have said on here because it is very important - Try going on dates with as many women as are interested in you. When I saw my boyfriend on a dating website my first reaction was "uh...I don't know..." He is a sports journalist, I am a mathematician. He is Jewish, I am totally unsure about my religion. I didn't think he was unattractive but I definitely wasn't taken away by the pictures I saw. I doubt he was with me either. But I figured what the heck and I swiped right and when I met him I was instantly attracted and we had so much to talk about. I'm NOT accusing you of this because you seem like a very kind guy but I know many guys who won't date someone who is even a little bit overweight or not as pretty but then complain about not finding anyone. Obviously being a little attracted to the person is important but even if you think she looks horrible in her profile picture some people just look WAY better in real life (like my guy). When I was on dating websites I swiped right on about 80-90% of the profiles to maximize my dating pool.

Also, I noticed that you work in Chicago. Maybe try dating outside of the city. It's annoying to live an hour away from the person you're dating but as a small town girl living in a slightly bigger town I will say that sometimes people in smaller towns (especially in the Midwest) are more down to earth. What are your filters set to on dating websites? Just increasing from a 25 mi radius to 40 or 50 can make all the difference. Or setting your age range from 34-42 to 30-44. Making your dating pool bigger gives you a better chance of finding the right person.

I also want to echo what Larissa_NY said in that I assume that you are a totally good and well-meaning guy. But if you come off as resentful for not having a wife by now or desperate or overbearing or needy or like this is an audition to be a wifey or like you feel like you have earned a wife, the woman is going to be creeped out. And again, this isn't about whether or not you ARE creepy. I think it is TOTALLY SWEET and well-meaning that you have saved for a family and a wife. It is about whether or not you COME OFF AS creepy. This is another way in which someone who knows you better could help.

Also maybe try seeing a therapist/life coach. They might be able to help you find fulfillment in other ways and see the things that may be turning women away.

It sounds like you're not getting past the first date and I think it's important to point out that dating sucks...like for everyone. And the big reason it sucks is because it's all a game of first impressions and that's hard. You saving for an engagement ring is so sweet but it may COME OFF AS creepy. You wanting to provide is sweet but it may COME OFF AS you expecting that she will quit her job to take care of your kids. Its all about what you come off as, which makes it harder. Even things that are much smaller than my examples above can make or break. This is where pseudo-dates with friends can really help you. But only if you tell them you really want their honest advice.

Coming off as very kind and gentle is important on a date. It's scary to be a woman sometimes. Especially on a dating website you are skittish because that guy could very easily be a serial killer or a human trafficker or etc. I too read the comment about your weight as not intended as derogatory. As previously stated, I am MUCH more attracted to big guys, but at the same time it did make me feel safer when I showed up to a date and knew I could take the guy if he got fresh. Make sure you are coming off as kind and respectful. Make sure you aren't crowding her space or jumping the gun on physical intimacy (even something like touching her arm - give her an hour or so to get comfortable and start feeling a base level trust with you). Also its so much more exciting when you're waiting for that physical intimacy for a while. Girls like a bit of a chase too so playing it a LITTLE bit cool can help your case.

Revisiting the non-negotiables. I don't think that you should give up on anything that really matters to you. However, in the dating pool that you are in cutting off previously married women or women with kids is cutting off a lot of people. Maybe you should revisit this and decide if it really matters to you. I.e. would you be happier being alone forever or being with someone who has been married previously. If you have this standard to avoid women with romantic baggage...well we all have romantic baggage. Divorcee or not. I understand feeling like you were being compared to previous husbands or that you were her second choice but maybe try going on a date with a divorcee and see. You may realize that even though you weren't her first, you were who she WANTED first but didn't know existed. And even though its her second wedding its her first with the guy she really wanted. If they divorced its likely that she would see you as her marvelous second chance. Speaking as someone who has been in two long term relationships - I appreciate my guy SO MUCH MORE given that I have a horrible god awful guy to compare him to. The comparison game would likely work in your favor, friend. Again, you could always just go on a couple of dates and feel it out from there. If it's something that is important to you then you shouldn't go back on it but trying never hurt anyone. That sucks that that girl kept comparing you to other guys but I don't think that would be the norm from most divorcees. But if you do decide to stick to no divorcees that is perfectly fine - maybe just make the dating pool bigger in other ways as mentioned above (age, location, etc.)

Also recognize that there is a large group of women who are attracted to older men. Your lower limit should be set around 10 years (or maybe more) younger than you are - if thats something that you are comfortable with.

Going back to the "coming off as" bit. Make sure the women you date don't just feel like you are looking for a wife. If they feel like any woman would do they are going to feel hurt and unappreciated. Even if you are going on 3 first dates a week try to make each one feel special.

If you are dating 6's and 7's they are much more likely to care about your personality than your looks so try to put away those inhibitions. Look good for a date but more importantly come with some meaningful questions. Make a good connection.

It might help if you see a psychiatrist about the depression you've been feeling. I have depression and anxiety and both of the people I have been in long term relationships with have depression and anxiety. However the first was entirely out of control. I had to take care of him constantly, it was a very codependent situation, and he turned it around into anger and abuse towards me. I'm not by ANY means saying you would do this. What I'm saying is that while depression is a totally valid illness it is the job of the person with depression to take care of themselves. It may be that women are picking up on this and decide that they really like you but don't feel prepared to help you through that. This may be coming off as callous but the reason I'm saying this is because my second relationship where we both take full responsibility for our mental health is much more healthy. Women may sense a codependency coming if they sense the depression and feel that it would be unhealthy.

Most importantly - you CAN find someone. You should realize it might take longer given your (valid) stipulations but you can find someone. Things will turn around. As much as it sucks try to spend this time on your physical and mental health so you can better attract the woman you're looking for.

You are to be commended for your hard work in making the changes you set out to make. That takes incredible perseverence and strength. OWN IT! Self confidence is sexy!

But now I’m going to be blunt: you’re playing the victim here. The world owes you nothing.

I met my husband online. Both of us had been married before and he has 3 kids (I chose not to have kids). It never even occured to me to compare him to my ex husband, let alone anyone I ever dated. Our interests and experiences prior to meeting ARE new to the one who didn’t go through them, so it is always “fresh” for one of us, same as it would be in any relationship. My stepkids are AMAZING! I cannot imagine my life without them. I brag about them every chance I get. Their parents have done a wonderful job raising them!

Please consider taking the advice already mentioned and be more lenient in your requirements, even if it’s only expanding the age range and/or distance. I’m from Chicago - I know it’s a big area. Also, please see a professional to discuss your concerns.