Dr. Reality Steve
Hi Dr. RS,
I don’t normally seek out a lot of advice when it comes to dating, but I feel I just need an unbiased man’s opinion on this. I’m 27 and started dating someone new. He’s 29 and currently studying for the bar exam – it’s essentially his full-time job this summer. We’ve only gone out a few times, but it seems to be going really well and I like him a lot. My only hang up is that each time we’ve gone out, I’ve paid my portion. I am pretty traditional when it comes to dating and I think in the beginning, when a guy asks you out, he should pay. Once you get into a relationship, I think it’s only fair that both people contribute and I have no problem doing that. But in the beginning, it just doesn’t feel like I’m being taken out on a date when I’m paying for myself. (To clarify, on the first date I paid for the tip because his portion of the bill was higher, but since then we’ve split it equally.)
I know he’s not able to work right now so his income is basically non-existent and I appreciate that he’s making time to spend with me during this busy time. I haven’t said anything to him about how I feel because I don’t want to insult him and come across as some greedy b. But I’m just disappointed that he hasn’t actually taken me out to dinner. It’s not something I’m used to.
So. I’m curious what your thoughts on this are. Is this something I should just get over? Is it a sign that he’s not traditional or just not very gentlemanly? How big of a deal is paying for a girl the first few dates?
Thanks in advance,
Comment: I’m amazed by how many emails I’ve received like this. It baffles me that not every guy out there is paying for every date. I do. And I know plenty of others that do too. I don’t get it. You ask a girl out, you pay. It’s pretty simple. If you’re having financial trouble, then don’t ask her out. It sounds like he is, so, this sounds like something that if you are going to continue with him, you’re probably gonna have to get used to.
Then again, I pay for everything all the time and it’s gotten me nowhere, sometimes not even a “thank you” or a fake grab to the purse to at least pretend she’s interested in paying, so maybe I should start acting like an ass and going dutch on every date.
There could be a number of reasons why he’s not choosing to pay. Has he said anything about it, or is it like the white elephant in the room? I mean, when the bill comes, he just asks you for your money? Or just assumed you’re paying? Wow. That makes me cringe just writing it. That sucks.
Hi Steve! I’m a long time reader of your column and look forward to it every week. I don’t so much have a question, but would like your opinion on my relationship. I’m a 40 year old woman who is in a year long relationship with a 31 year old guy. That being said, I was just wondering if you have any thoughts on older girl/younger guy relationships. I was married 10 years ago, that marriage lasted less than one year but produced a beautiful little boy. I had a really tough few years in between these two relationships and actually this is the first serious relationship I’ve been in since my divorce. My guy now treats me well, is kind to my son and overall we are happy. I guess what I’m kinda looking for is your opinion as to if you think this could work. Initially, I never wanted to get remarried but as this relationship progresses I find that my mind is changing. He also says that he would like to get married. More children is out of the question (not medically, but i’m just done with that!). I don’t know – do you think eventually he will want a younger girl? He’s extremely good looking so sometimes I just don’t even understand why he’s with me. I guess I am just looking for an honest opinion. I hope you are well and keep up the good work! 🙂
P.S. – Oh yeah – one last thing – he doesn’t have any children and says he doesn’t want any – I think he may change his mind.
Comment: Seems like you’re dooming the relationship before it even starts. I know the feeling. Obviously there’s plenty about your relationship I don’t know about, but why don’t you think you’re able to pull a guy 9 years younger who’s extremely good looking? Don’t sell yourself short. You’ve been with the guy a year, so it’s not like this is brand new or something. I could see you having those doubts if it was early on, but he’s lasted a year, so I’m not sure where your insecurities are coming from. Seems like you’re on the path with him as far as marriage and kids, so what’s the hang up? And what makes you think he may change his mind about kids?
Either there’s more to the story than you’re not telling me, or, you’re just paranoid some guy is gonna leave you because I don’t see where this is coming from. You’re a year in. Sounds like it’s going well. I think you’re just being paranoid that he’s younger and good looking. Who knows? Maybe he will leave you for a younger woman. You don’t know that. I don’t know that. Any guy could leave any girl for any BS reason whatsoever in a relationship, and vice versa. So sitting around waiting for it to happen isn’t helping you much. I speak from experience, even though it seems to happen to me every time as well.
Dr. Reality Steve,
Hey Steve! Okay I’ve got an issue, and I would love some outside insight. I have been dating “Andy” for quite some time, and we’ve started talking about marriage pretty often lately. I am so happy with him, and I think we could have a great life together. The problem is my best friend.
“Jessica” and I have been best friends since high school. We have all the same friends, and we spend quite a substantial amount of time together. She is happily in a relationship that is also at the point of talking about marriage. Unfortunately she has made it pretty clear that she doesn’t think Andy is right for me. She goes on and on about how we have different personalities. He has a very dry sense of humor, and is very sarcastic (I feel like you can relate), while I am very reserved and sweet. Jessica and her boyfriend are very similar to each other. They have the same sense of humor, they’re both very goofy, etc. I think that is great and I have always supported their relationship, but I can’t seem to get it through her head that it doesn’t HAVE to be that way. I have seen so many successful marriages between people that have different personalities and interests.
I should add that my family loves Andy. He has good morals, a great career, and just a good head on his shoulders. I am the youngest in my family, so we’ve spent a lot of time with my siblings’ and their spouses and kids. He gets along with all of them so well. So there are no red flags or any major reason why he shouldn’t be right for me.
I am just really not sure what to do now. I have tried talking to her, and she ends up saying she agrees. Now she just acts like there is nothing wrong and she’s “so happy for us.” But I am constantly hearing about what she said to another friend when I wasn’t around, and anytime I try to get us all to hang out together, she has some reason that she can’t make it. I would think there was some jealousy issues behind it, but she has her “perfect man.” It is just so frustrating that she can’t even give Andy a chance. I shouldn’t have to choose between my best friend and the man I love. I can’t have a maid of honor in my wedding that hates the man I’m marrying. Any thoughts Steve?
Comment: Yeah, without knowing anything about Jessica, it’s hard to see where she’s coming from in this one. My first answer would’ve been she’s jealous of you, but that was shot down when you said she’s in a relationship of her own and talking about marriage. Although, there could still be jealousy there. Maybe her relationship isn’t all it’s cracked up to be and she’s hiding stuff from you, and she actually sees YOUR relationship as better than hers, so she’s trying to bring you down. Is she the competitive type? When you guys were talking about your respective relationships, whose potential marriage got brought up first, yours or hers? Maybe she wants to beat you down the aisle? Maybe she really isn’t close to getting married, but just saying she is to make you think she’s got a great relationship?
If she’s your best friend, and she’s the only one in your inner circle that doesn’t like your boyfriend, there’s got to be a reason other than “your personalities are different.” Your family likes him, you like him, your nieces and nephews like him, but your best friend doesn’t. There’s something she’s not telling you because that reason doesn’t make much sense. Does she really hate him, or she just doesn’t care for him? Has he ever talked to her about it? Is he aware your best friend doesn’t like him? I get that maybe she’s concerned for a friend who’s with a guy that maybe she doesn’t feel is right for her, but she needs to get over it if you’re happy. If she can’t, then you tell her that her attitude is making it more and more difficult to hang out with her. If she can’t deal with that, then you probably need to take a break from each other. If she hasn’t come around by wedding time, then I don’t think she’s much of a friend.
Dr. Reality Steve,
So, I met this guy at my cousin’s wedding in December (he was the Best Man). We instantly connected and became friends real fast. He was so easy to talk to and seemed to have all the qualities I ever wanted in a guy. We work and live in different cities so most of our friendship was developed on long telephone conversation calls (some times as long at 4-5hours daily). In the first couple of months, he would call me really early in the morning, during the day and late at night. I wasn’t sure what he wanted from me exactly but I was always there to pick his calls and respond to his text messages. He would tell me personal and intimate things about his work, friends, relationships and family but he never said anything about having a girlfriend. He would flirt and call me all sorts of pet names. I traveled to his town on a business trip a couple of times; we met up at his apartment both times, just had lunch, watched TV and nothing else.
After a couple of months, the calls became less frequent sometimes once in three days. I was initially unsure why but assumed he was just going through a hard time at work. At this point I had gotten so used to his calls and messages that I felt like I was missing something. Sometime recently (known him now for a total of 6 months), I was tired of the mixed signals and wanted to know if he liked me or not so I could move on. I wrote him a note (emailed it to him) highlighting our journey up till that point and told him he occupied too much of my thoughts which came up at random, uncontrollable times and I had no idea what to do with them.
He responded by saying, he was sorry and that all he wanted was friendship and nothing more. I was shocked because I was absolutely certain he liked me more than a friend. I couldn’t believe he had spent that much time and told me all those things if all he wanted was a friendship. I am absolutely certain there is no way he could afford to give that amount of time to all his female friends. Anyway, I kept my cool (even though I was hurting inside) and told him it was alright. He still calls me late at night and sends text messages during the day. I really don’t know what to do but I know I have to move on because he seems confused right now. I need help deciding whether to hold on or stop picking his calls?
Comment: And he hasn’t mentioned anything about dating anyone in the last 6 months? There’s gotta be another woman in the picture. No one would spend that much time talking to another woman about the stuff he talked to you about if he wasn’t interested in something more. You just don’t do it. Guys aren’t wired that way. Unless he’s gay and wants a female friend, then yeah, I could see it. But by what you described, to me it sounded like he was interested in you, but something came along more geographically desirable to him, and he went with that.
Props to you for coming right out and telling the guy, “Look, what the f*** are you doing” and at least forcing him to give you answer, regardless of how full of sh** I think it is. I’d keep the texting and calling to a minimum from here on out. You told him how you felt, he said he wanted to just be friends and nothing more, so there. Unless you want to continue to be this guy’s sounding board, just keep the communication at a minimum.
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