SJC2008 Posted December 22, 2019 Share Posted December 22, 2019 (edited) I'm a man in my late 30's and have never been married and have a mega crush on someone who's been divorced twice. Should we all get our popcorn ready? lol. I've heard through the rumor mill at work that she's interested but I'm so embarrassed of my relationship history I can't seem to overcome it/ bring it up. It's been a long time since I've posted here so here's a quick recap on me. I'm very shy in the women department, never had a lot of success and have had no serious relationships. That being said I'm not a virgin or a "stick in the mud". I've experienced some things like making out in a car where it got pretty sexual, a one night stand (one), and I've had sex on a beach in the middle of the night. Those aren't my things per say I'm just trying to give some background in that I'm not a total wallflower. Besides the shyness, while I'm a college graduate and have a great career that pays moderately well. I have a lot of debt and my living situation isn't ideal for my age, especially when it comes to dating. I'm not broke, I do I have some spending money and am working on getting out of debt. Anyway, I do feel I've dated enough to know what I'm looking for and what my issues were. I used to gravitate toward controlling women and have also learned that I have a severe intimacy issues getting close to someone. As corny as it sounds I feel like I am ready to give my heart to the right woman and have kids; And from what I hear she wants kids so this would be dating with the intent that we are looking for something that could become serious. So how do I tread this? How the heck do I tell her my history and hope she's OK with it? Also, I HATE the fact of dating a co-worker. I've avoided it for 21+ years because my 1st girlfriend when I was 17 humiliated me at work. I don't need my history on bulletin board if you will. Lastly, while my non-history is baggage she has the opposite baggage with two failed marriages so I have serious questions of my own. Edited December 22, 2019 by SJC2008 Link to post Share on other sites
Versacehottie Posted December 22, 2019 Share Posted December 22, 2019 (edited) I think you can't get too hung up on your "history". If you are right for each other, it won't matter too much. So focus on if you are right for each other and the connection you have. Don't judge her by her "history" either. That's the thing about history. One could say that her experiences may have taught her how BETTER to approach relationships and what she is looking for for real. In other words, you can look at it positively or negatively. It's all in perspective and how you present it/yourself. You can't change the past, in terms of you can't go back all those years and change the outcome of what happens--the only thing you can change is your perspective on it and how you use it to mold your own opinion of yourself and how you present yourself to others for their opinions to mold. IMO, there isn't much of a need to present it as a negative. Some girls will appreciate a guy with no ex drama, and that the relationship you build together will have many of firsts. For this girl, it's a chance to "get it right", etc. IMO, also I'd be more concerned that you are someone who let an incident with a past gf so many years ago, prevent you from moving forward with things you want and left you SO guarded. That I think you should ACTIVELY work and and express/show that you are being more open, not shutting down this extremely when you feel hurt. I think the most attractive thing you can do with the situation you are dealt with right now is also express and consistently show to her/the world and most importantly yourself that while you recognize where you "are" in terms of living situation, debt, inexperience with women that you are ACTIVELY growing yourself and committed to a plan and taking steps to move your life in the direction you want. That will erase many people's judgement of your "history". Most importantly, i think YOU will find your "history" much less limiting when you are consistently and constantly in the present changing your situation and expression of yourself. Good luck Edited December 22, 2019 by Versacehottie Link to post Share on other sites
Versacehottie Posted December 22, 2019 Share Posted December 22, 2019 Ooops, forgot to say, I agree that dating a co-worker can be tricky. I think when a person is on the extreme end of the spectrum, i.e. more closed off or too quick to jump into relationships, it can prove EVEN trickier since being on either of these ends of the spectrum may up the odds that it doesn't work out. You can combat that by taking the slow and more cautious approach of getting to know her BEFORE you start dating. This would allow you to feel more secure and comfortable opening up and build assurances that dating her would be less likely to backfire. It also gives you a chance to see that if she is not right for you that you don't progress something that shouldn't be progressed. Link to post Share on other sites
Lotsgoingon Posted December 23, 2019 Share Posted December 23, 2019 Your main task isn't about how to come off as socially experienced with this woman. No. That's barking up the wrong tree, one with no acorns. What you want to do ... your task ... is to get clear with yourself ... and accept yourself. You're making some vast assumptions here ... People, whether they have been married ten times or not at all, are looking someone they enjoy being with. So I don't accept your premise that she has the baggage of two divorces or you the baggage of not dating much at all. As for your life and your salary and your money--YOU have got to make peace with that. If you bring all that insecurity into dating, you're setting yourself up for failure ... because you walk into the room already feeling like you need to hide and apologize. You need to write out a list of your strengths and your good qualities ... you need to identify interests and hobbies and passions ... you cannot step timidly into a dating. I get it ... I have a great job ... that pays a modest salary ... and there's a lot of talk about women wanting men with big money and all of that ... yeah yeah ... and men like beautiful women ... In the vast middle, we date people who appeal to us ... who aren't rich ... and aren't Cover Girl models. You're looking for a woman who can appreciate you and your strengths as you are right now. BTW: moving in a good direction and working on yourself and growing ... can be part of who you are. This problem probably knows exactly how much (little) dating experience you've had. You think this is something you can hide--not really. People intuit that stuff--comes through in our body language and how we act ... And apparently, she is fine with that. No surprise. People don't find people they like and then say, wait, but you haven't dated much! ... Do some working on yourself and your own confidence ... and acceptance ... go to therapy if you have to. But trying to find a strategy or some tactics to hide your baggage is off course. There is no baggage to hide. Link to post Share on other sites
Brennan72 Posted December 23, 2019 Share Posted December 23, 2019 I don't think there is anything wrong with your past. Obviously she is more "experienced" than you, but that is about it. But I would worry a whole lot about getting involved with a woman who has ben divorced twice. I had a buddy do that, and she took him to the cleaners. I think she is on husband #4 now. There is a reason why people end up divorced multiple times But if you really feel like you need to test the waters here, you can take her out a few times, maybe date for a bit, and get to know her better. You can ask her about her prior marriages, why they fell apart, what the expectations were, etc. You can also get some info on her sexual past. If she is vague, or refuses to divulge meaningful information, I would break it off immediately. You can't go into something like this blind. There may have been domestic abuse, cheating (on her side), and who knows what else. Link to post Share on other sites
Kaarek Posted December 31, 2019 Share Posted December 31, 2019 You seem like a pretty chill down to earth guy so I'll try to be pretty honest with you about a few things. Women ADORE confident men that has their thing going on, you have debts? Well, who cares! Everyone has issues of their own, that's not the big deal in this topic but your attitude is! No woman likes men that feel bad about themselves, highly insecure and not "intimate" enough. Some women might put up with your insecurities and stay by your side (but wont stick around for long, trust on me that!). What you have to ask yourself is this: Would you date an insecure woman? Someone that doesn't know what she "really" wants? (I am not saying you're a horrible human being and you shouldn't date anyone ever, take it easy but you can better yourself, you just have to change your mindset). Integrity, Confidence and Listening are three things that most women look for in a man. I am not trying to offend/lecture you by any means, I hope you didn't feel so but man up SJC and don't think too much about what could go wrong. P.S. Confidence isn't Arrogance (some think being confident is becoming a cocky person, not at all!) 1 Link to post Share on other sites
CautiouslyOptimistic Posted December 31, 2019 Share Posted December 31, 2019 On 12/22/2019 at 2:58 PM, SJC2008 said: Besides the shyness, while I'm a college graduate and have a great career that pays moderately well. I have a lot of debt and my living situation isn't ideal for my age, especially when it comes to dating. I'm not broke, I do I have some spending money and am working on getting out of debt. How did you acquire so much debt? Is it student loan debt or did you make some poor choices you're afraid to tell a future partner about? What is your living situation? Link to post Share on other sites
Author SJC2008 Posted January 5, 2020 Author Share Posted January 5, 2020 On 12/31/2019 at 1:37 PM, CautiouslyOptimistic said: How did you acquire so much debt? Is it student loan debt or did you make some poor choices you're afraid to tell a future partner about? What is your living situation? Student loan debt and I got out of control with credit cards and am regretting it. Most of is was from when I was younger, using credit cards to sustain a lifestyle I couldn't afford. I live with one of my parents and pay my share monthly. The debt is not good but it's not my main concern. I have good credit. My main concern is my R history and living situation as said. 1 Link to post Share on other sites
CautiouslyOptimistic Posted January 5, 2020 Share Posted January 5, 2020 2 hours ago, SJC2008 said: Student loan debt and I got out of control with credit cards and am regretting it. Most of is was from when I was younger, using credit cards to sustain a lifestyle I couldn't afford. I live with one of my parents and pay my share monthly. The debt is not good but it's not my main concern. I have good credit. My main concern is my R history and living situation as said. Yes, living with parents in your late 30s is not a good look, I'm afraid. 1 Link to post Share on other sites
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