Single Mom & Paying on Dates?!?!

I don't get it, why can't you just talk to him about it? If you aren't able to talk to him, then why are you even dating him?

"Hey, going forward do you think we could go dutch? Money's a little tight for me right now."
Seems pretty simple to me.
It's called honest communication, give it a try!

Talk to him about it.

And if you can't talk to him about something as small as who pays for a date and you've been seeing him for 8 months, something isn't right with that relationship.

I think there's only one way to get the sick feeling in your stomach to do away...

end the relationship.

Think about it, if you can't be open and honest about living frugally, what sort of relationship is this anyway? Relationships require mutual trust, first and foremost.

It sounds to me as if A. you don't trust this guy not to dump you if you are honest about this or B. you don't trust that this guy is sincere and not using you.

Either way, a sick feeling in the stomach is your gut talking. Listen to that little voice. My guess is that this isn't really so much about the money as it is that the money represents something that's really wrong in the relationship which is the fundamental lack of trust and lack of any substantial communication. Both of these are essential to a healthy relationship. I'd say it's time to let him know what's what and let the chips fall where they may-- at least you will know where you really stand.

Sounds like it is time to end the long distance relationship.

He waited for you to mention any sort of payment and now he expects it. Just think, if you marry him, it will only be worse.

I think the sick feeling in your stomach is telling you what you need to do.

Maybe he is tired of the on and off relationship and senses that "you just aren't that into him" and he's tired of whipping out his wallet on someone that isn't that serious?

This is what you wrote: "when we were "on" during that time- he would pay(I really wasn't that interested at this time) and I wouldn't even think to offer. "

So when you weren't interested you "wouldn't even think to offer"???? Why not?

I was a single mom, had a mortgage etc etc and I still always offered. It was always refused but I would buy tickets to an event so I could *help* pay my share. I never wanted to look like I was a moocher.

How far is this long distance relationship? If he's traveling to see you, then maybe you should pick up some of the expense.

Everyone has their expectations. If you know he doesn't make a lot of money, then yes, you should chip in.

I'm sure you will figure it out.

here's my honest answer: that sick feeling in your stomach is your WiseWoman speaking to you.

Dump him.

Stop offering to pay and stop saying you want to go somewhere. Let him make the offer to go places, and let him pay.

I'm old fashioned. The gentleman takes the lady on a date, the gentleman pays.

Should you suggest an activity, ensure it's a cheap one that you can easily afford. If he asks about the change, explain that you simply cannot afford to foot the bill for all the pricey outings and have put yourself on a budget.

ETA: Also, I think it's rather concerning that this guy has a history of failed relationships with women who always foot the bill...

RED FLAG.

I am all for women towing the line. I've done it plenty and have always split at LEAST 50/50 in every relationship until I finally gave birth at age 35, then I allowed myself to be supported by the father of my children (who I had been splitting things with for 4 years before our first was born) for the first time in my life. BUT. Now, as the mother of 3, I would not personally become involved with a man who needs my financial support in ANY way beyond gifts and treats I want to buy him. If I get a high-paying job one day, that may change, I may chip in again within the right relationship, but in general as of now, no.

I am confident enough to remain alone, and if I want to share my life with someone, he has to be financially stable and more importantly he has to be a generous person who WANTS to support a family. Things can be so different for so may families. If people grow together sharing expenses, that's great. If my ex and I had not divorced, I would have gone back to splitting things as able.

But at the BEGINNING of a NEW relationship, when you already have kids you work hard to support, do you really want a guy who does not LIKE to pay for things? That speaks volumes to his character, and it will not change!

I was recently dating a very low-paid teacher. Financially, it actually could have been OK because he was SO generous and hard-working. He NEVER let me pay for dates. He NEVER let me pay for sitters. He was always willing to drop everything to help me and bought stuff for kids on holidays etc...we split up for other reasons, but he would have been a hard-working and generous caretaker, so it's not about gold digging. It's about WHAT KIND OF MAN is comfortable with you paying all the time?

When I look back at the men who let me pay happily I see now with more maturity that it was NOT a good quality then, and it certainly wouldn't be a good quality now. Especially in a relationship that could potentially become a role model for your kids.

I don't like how this guy sounds, sorry. You did not work this hard to support a guy like this. Your gut is correct. I would not be getting "more serious" with him as he acts worse and worse about money.

Be DIRECT. You don't sound like you have a mature honest relationship at all if you can't say, "Hey, I'm actually not able to pay for so many things. I'm already on a pretty tight budget supporting myself and my child(ren). This relationship is starting to be hard for me to sustain." If he's kind and cares about you, he'll respond honestly and helpfully within his means.

Or start making comments like,
"I can't afford to go, sorry" and don't be available. See if he steps up. His past is an indictor of future trouble though. Your kids don't need a dad like this.

he doesn't sound like such a great prize. i don't think it's expected that men should always pick up the tab, but if it hasn't been discussed, it also shouldn't be expected that you always will.
big red flag for me that you're not comfortable discussing it.
also that you already know that he's kind of a big baby when it comes to sponging off women.
and that you have a sick feeling in your stomach.
i think i'd lean toward 'off again for good.'
khairete
S.

Why does a walk in the park require cash in hand?

If the two of you are in a serious relationship, you should be able to discus what you can and cannot afford.

You don't feel good about this situation. Listen to your instincts. They rarely steer you wrong.

When I met my husband, he had a much better job than I did. He was 35 and established in his career. I was 23 and just starting out in my career. Our second date, I informed him that I'm high-maintenance, and as fair warning, I was raised to expect a nice man to want to pay when we went on dates. He said, "I doubt you could be any higher maintenance than my sister." And the rest is history! We celebrated our 15th anniversary recently. Anyway, I would be put off by any man who didn't reach for his wallet when we went out to dinner, unless I had done all the asking. But if it was something we mutually agreed to do, or if he had asked me out to dinner, he should pay. Maybe once in a while, as you're able, you could leave the tip, or pay for drinks after dinner or something. I know I'm old-fashioned in this regard, but I worry about a man who doesn't want to take care of you BEFORE you get married! He's on his very best behavior right now. Think about that...

My father taught me a long time ago that it's okay to stay home if I don't have money to be out. In fact, he taught me that I should stay home if I can't afford to be out. A (sometimes) boyfriend does not equal a bank account for you. You should not suggest going out unless you are prepared to pay for going out. That's with ANYONE. Otherwise, you're planning how to spend THEIR money, and no one likes that.

As a single person, you should be prepared to either pay for yourself or stay home. Being invited out and "sponsored" on an outing is a privilege, not a right. If you want somebody who believes that you shouldn't have to pay, then go out and find that guy who also wants that.

ETA: About the other women, you THINK, but you don't know. Don't hold it against him that he seems to know how to get what he wants.

I think that your idea of dating is pretty outdated. Your a grown woman...why should he have to be the one breaking the bank to maintain a relationship?

I was also a single mom, and about your age, when my husband and I started dating. He paid for dinner on our first few dates but after that, it was natural to split things...sometimes he would get the check, sometimes I would. If I planned an expensive night out (going to the ballet or a concert), then I bought the tickets. We both earned about the same at the time, both had bills to pay, we were both single parents...why on earth did he owe me meals and entertainment? Now there were some thing that he had the means to pay for an I didn't. He had an inheritance that was generously supplementing his income so when he wanted to go to Miami for a weekend, I had to be honest and say that it wasn't in my budget so he sprang for the trip because he could afford it and wanted us to go.

After 8 months, you should be able to communicate openly about money. Honestly I think the fact that is hadn't even occurred to you to offer to pay when you were first dating this guy is pretty clueless and self absorbed, and the fact that you want to enjoy events without paying for them and want to break up over it is perhaps a sign that this is not the guy for you. But really, if you want to date, you have to expect that yes, it's going to cost you money as well to go on an outing.

If you're thinking about becoming serious with him, you need to be able to be honest about finances. Let him know it's getting tight for you and you need to start going dutch. In this day and age, it's crazy for any one person to be paying for all of it anyway.

Long distance? Who is paying for the travel? How far? If I were traveling any long distance I would expect the host picked up the costs while there and I would pick up the costs when they visited with me.

Still if you are not communicating your needs you can't exactly blame him for not knowing them.

You need to have a conversation with him the next time you talk to him.

His response will tell you what to do next.

It sounds like this is not your expectation of how a relationship should be. Maybe you need to consider this. Maybe that is why you have a feeling in your stomach :-).

Keep us updated.

Best of luck to you

I haven't read all the answers but the first thing that comes to my head is; just be honest with him. It's bothering you, so if you are in a relationship you should be able to talk to your partner about anything. That doesn't mean no one will be hurt, but you both will be on the same page and don't have to "wonder" anymore. Just be honest with him and go from there.

By the way, my opinion on relationship besides being honest, it's 50-50. Now it doesn't always happen that way, but I think each person should be doing their part and no one should be doing all of one thing. This doesn't apply to just paying for things either. Maybe one is better off than the other, there are other things the partner can do to make it 50-50; partnership.

Never paid for a thing and never thought about it? Before this relationship you never thought to be giving and generous?? I bet it was fun without a care in the world. Stop suggesting wonderful trips or leave the old wallet at home again.

Exactly what Mamazita said. When you offer to pay and he takes you up on this, that is not 'taking advantage'. Also, when you suggest going somewhere, it is perfectly reasonable for him to expect you are paying. As long as when he suggests a place, he is paying. I cannot believe that you have never paid on a date. I truly cannot believe it has never even occurred to you to offer before. I know Fayette county is the country but I am shocked.

ETA - Is the queasy stomach feeling because you don't want to talk about money (because you need to get passed that, any relationship you have in the future is going to involve $$ and most men are NOT going to expect to pick up your child's expenses, your mortgage or anything more. You need to be able to talk about the little date expenses before you get to the big long term relationship issues)? Or is the queasy feeling - you don't like talking to this particular man any more - if that's it, maybe it is over - but then you seem to say you see potential for a longer future (cooking dinner).

I'm not sure how to undo this, but I do think there is a silver lining here. You understand and know something very important about yourself; you are traditional and function better in traditional roles. They make you feel valued, cherished and loved. You want a man who wants to be a provider, you want to be supported in this way and you want to support a man in other ways (and there are many other ways).

I agree that being out and about complicate things because you cannot reciprocate by cooking for him. There are also lost of other factors like his financial status and how long you have been dating and if this is really courting or just passing time.

I would say the issue here is deeper than wanting him to simply pay for dates because your "funds are low". You may not be compatible with your preference for gender roles in general. Perhaps on a deep level you don't see eye to eye on gender roles at all. And in the end this could really complicate things.

Perhaps he feels as uneasy about the arrangement as you do. Perhaps he dare not turn your offer down, though he also prefers traditional gender roles.

Let me briefly relate a story from my dating days that profoundly made me feel for all the gentlemen trying to date the modern woman. My last dating experience before meeting my now husband went like this: On out first dinner out he made it clear he had no problem with the woman paying. ( I knew instantly he was not the one for me. ) He then relayed a story of trying to pay on a first date and having the woman slap him across the face she was so insulted (talk about a confused woman: "don't treat me like I'm helpless, now here let me hit you in the face because I'm the weaker sex, but don't' hit me back because I'm just a helpless little woman!"). In any case, I knew right then and there he was not for me. At the same time, I felt enormously sorry for this fellow and all men trying to date in the modern age. On one end of the spectrum you have women who are offended if the man offers to pay, and on the other end of the spectrum are women like me, who wouldn't dream of marrying a man who did not demonstrate from the get go that he was more than willing to be the financial backbone and provider.

Better talk it out with him and see where he's coming from. This has deeper implications on compatibility in general on male/ female roles. If you lean traditional and he does not it affects every part of your life together, not just financial.

For many years now when dating we've shared the bill. If I were seeing one person I would either go "dutch" or alternate who pays. "Dutch" means each pays their own. When I was married, each of us had an income, sometimes I'd pay; sometimes he paid. We had separate checking accounts. We shared living expenses including entertainment. I suggest that with the advent of women having an income we're getting away from men paying for everything. If the man has an income why should the woman pay for everything?

If you haven't discussed this with your boyfriend it's way past time to do so. Money is frequently a big dividing issue in marriage. I suggest agreeing on who pays at the beginning is important before the relationship reaches the serious stage.

I think you have learned or are learning a valuable lesson here.

The sick feeling in your stomach is telling you something isn't right.

If I were in your shoes I would kick him to the curb. Life is too short to spend your valuable time with someone whose actions or inaction makes your stomach go into knots at the very beginning of a relationship.

Time to move on to new ground and if you aren't the kind of woman who wants to and can afford to pay for dates in the future just don't do it. Keep things simple.

Don't offer.
Just stop.

What I do not see is how you feel about this man. No mention of that at all.

If YOU feel like you want to treat, just do it. Buy the tickets, grab the check. Why all the discussing?

IMO, if a man wants the pleasure of a woman's company? He expects to pay. If she chips in? Bonus.

I have a couple of things to think about... they may be repeats as you already have 38 pieces of advice below :)

1) You are comfortable explain your financial situation to US, a bunch of strangers, but not to the man you are dating? If he's worth a relationship, you should be able to say, "hey I can't afford to keep doing so many expensive outings, let's just hang out at home and make dinner in."

2) If YOU are the one saying you want to go somewhere or do something, it isn't unreasonable for him to think you are INVITING him! Good grief! Are you bringing up expensive excursions that YOU DON'T WANT TO PAY FOR because you want HIM to pay your way? It would be different if he approached you and said, "Let's go see a show, what would you like to see?" Then he's inviting you and you're just picking the show... but if you initiate "Hey, why don't we go to the Philly's?" You're asking him out then expecting him to pay, that's not fair.

You can't have it both ways. When I was dating my SO, he always payed for everything, including vacations, but that also meant I had to wait to be invited, and go on the dates I was asked (hip-hop concerts not ballets), and find something I liked on whatever menu was placed in front of me.

Hope it all works out for you.
T.

"We have a long distance relationship so when we do get together, we are out and about doing things, not just cooking dinner and going for walks (which I hope one day we get to that point)"

That's really sweet! Why not let that day be today? The next time he visits, cook for him and suggest taking a walk. Nothing wrong with that, and I don't see why it has to wait.

But saying you have a sick feeling in your stomach is not something to take lightly. I would really take some time to think about what's causing it.

To be honest, you're both wrong. He shouldn't expect you to pay, and you should expect to have cash with you no matter where you go. I don't know that you need to request separate checks at a restaurant, but it should be about 50/50.

Not clear - you always now pay for both of you? I definitely started chipping in once I was dating someone a while. Didn't seem fair for the guy to always pay even though I'm pretty traditional. I was making a very good living. But I'd never have gone along for paying for both of us all the time. Why not stop suggesting you go somewhere. Doesn't he make plans too? Does he make plans and then he pays but when you suggest then you pay? Or he never suggests so now it's all you?... 50/50 seems fine. If that's not the case, I'd break it off or stop suggesting outings and see what he does. Definitely weird if he's letting you pay all the time. He must know you're not rolling in money and even if you were, not a good sign for a guy to be taken care of by a woman...

Oh.hell.no. Time to go. Good luck!

So when he comes to see you or you go to see him -- you pay for everything, whether you in your city or in his? Is that the deal? Or does he only come to where you are? I'd like to know.....

Are you not only paying for every outing and meal but also planning them all? Does he make any suggestions or book any tickets or make any reservations, ever, or does he just arrive (or let you arrive) and then wait to be told by you where you're both heading?

Have you tried simply telling him, it's your turn this time to plan the weekend, period?

Next time he's due to visit you, I would say, "Hey, this weekend, I'm leaving it up to you to plan the activities. Here are a couple of web sites with 'out and about' stuff on them. I'm not going to plan anything at all, because I'm [really busy with work, have to be out the next few nights, whatever is true]. Last time around I found the X and Y activities and booked those tickets myself, but this time, if you want to do anything like that, please feel free to book it."

Then see what he does.

I had a long-distance relationship for a couple of years before we got married and neither of us would have expected the other to pay for everything, all the time. Ever. My now-husband liked to pay for certain things to ensure that our visits still felt like "dating"! But I also did not expect him to plan and book every single thing we did, nor did he expect that of me when he came my way. This was in the ancient era Before We All Had the Internet, but we were both still capable of picking up telephones and working ATMs for ourselves to plan things.

If your boyfriend is completely passive and waits for you to plan everything -- not just pay for it all, but suggest everything -- wow, I would move on. It's not just about finances. If he's just limply letting you do everything for him, he has zero initiative, and to me that indicates a lack of imagination about ways to spend time with you. He should be wanting to please you with things that interest you, if he's truly into you; if he shows no initiative in planning stuff at times -- he's not interested in pleasing you, is he?

If you don't feel good about being with him anymore then stop seeing him.
You need someone more local.
Long distance relationships can work but this one isn't and it's time to end it.

I would not feel comfortable with the fact that he expects you to pay and does not say anything about it. He has a history of letting women pay for him and maybe he kind of expects that. I would start a conversation with him that you are uncomfortable with the fact that he seems to expect you to pay. I would be honest and say my whole life when I am dating a man, he usually pays for me and won't let me pay. I find it strange that you never bring it up. Then see what he has to say about that. In the long run this guy might not be the best guy for you. My dad's sister married a man who has always expected her to work full time while he stays home. He did not really help with child rearing. He did not really even do job searches. He seems to lack any drive. They are both almost 70 and he never changed even though she wished he would. She supported him and their 3 kids their whole lives.

I agree with most everyone on here and I also think that it is commonsense for you to always have some money on hand-no matter who suggested the outing. So if you went to a ball game that was his suggestion and his treat-you wouldn't even think about buying a beer and a hot dog as a thanks!? I think that is pretty cheap of you and vice versa.
If you suggest an outing-you pay for part and he chips in on part-dinner and a movie-he paid for dinner-you treat for the movie. Or if he says he wants to pay for the whole night-at least buy the popcorn and soda-for goodness sakes.
I just think your statement about going on a vacation and not even taking your wallet is sad and scary. You feel he is taking advantage of you if he does this-how do you think your past relationships felt at your total lack of monetary contributions??
I am not trying to be mean-just saying I think it is always a two way street.

If you can't be honest with him, and you're feeling used, this probably isn't the guy for you. Tell him, and find things to do that are cheap or free. If he can't handle it, let him go.

"I just need advice and want this sick feeling in my stomach to go away."

Then break up... Unless you communicate to him this will not change.

But you have 20th century expectations and you live in the 21st century...just sayin'.

I will freely admit that I am old fashioned and I don't think there is anything wrong with that.

When my husband and I were dating he paid for everything. We did get to a point in our relationship that he just couldn't afford to take us out for the movies or whatever several times a week, at that point I offered to help. When I threw in money he would kind of sheepishly ask me in the car if I could give the money to him so he could "pay". He felt he should be paying for everything but he just couldn't afford to.

Sounds to me like your fella is a bit of a mooch and I'd give him the boot. You have a nagging feeling because you already know what you should do. I think finding someone that is nearby would be better for you and probably better for your child.

Look for a gentleman, they are out there.

M

If you he wants to do something and you can't afford it, tell him so. I always paid my own way when I was dating my husband early on. I didn't want him thinking he was going to be getting something for it- if you catch my drift. As time went on, I would pay our way sometimes, and other times he would pay our way. I had no problem with it. But if you do, you should tell him.

1)that sick feeling in your stomach is called your intuition, or god telling you your on the wrong path. Run for the hills.

2)woman shouldnt pay anything if the man really likes you he will never let you pay.

3)long distance relationship means there is no relationship cause if he really liked you he would do whatever possible to be closer to you.

4)good luck

I wouldn't want another "child" to care for (especially at the expense of my actual children) and that's what he sounds like from what you have posted.

That sick feeling in your stomach is probably your intuition.

Listen to your gut. If you are comfortable going dutch, or indeed often footing your/ and his bill, then it can work for you.

Sounds like this financial arrangement is proving too expensive for your taste, and is not in keeping with your budget. Also, it isn't in keeping with your expectations of money in a relationship (you want to be taken care of and paid for).

Speak with the fellow, let him know that you are uncomfortable with this arrangement. If he's happy to wine and dine you, great. If he's happy to go low budget, great. If he expects you to continue chipping in, and to pay for him too, then you'd best re-think if you can afford this relationship.

Best,
F. B.

Is he cheap or maybe going through a hard time financially? If you think he is someone you can see yourself with longterm than I would have an open discussion about this and see what he says. If there are other things that turn you off perhaps it is time to move on. My husband was going through a hard time financially when I met him (small business owner crappy economy) so I often offered to pay. We ended up splitting most expenses. I knew he was a hard worker and great guy so I wanted to pitch in. If I thought he were cheap or being thoughtless I would have bailed. He hated to have me pay at times but I talked him into it.

Maybe Im old fashioned but the woman should never have to pay for anything. If you are in a solid relationship (not just on and off and not long distance) and get to the point where you are staying home and playing house together after 6 months or so then its ok for you to offer to pay every now and then just for good measure. I hope you aren't intimate with him as well.

I think you might enjoy the powerful feeling you get when you invite him out and then pay, it might be a rush for you to think you are in control. The fact that you are involved in a long distance relationship tells me that you don't want true intimacy and perhaps are afraid of getting into something real. So again, a control issue. The fact that he allows this means that he is a child because no real man would be comfortable with this situation. Trust me, Ive been there. You're a single mom and proud to be self sufficient, a self assured man might intimidate you.

Guess what, this guy is in control because he's getting a free ride. Has he asked you yet how you feel about stay at home dads, because he will. Dump him! Find someone who is close by, who invites you out and wants to spend time with you holding hands and walking, and who pays. Yes, you will feel vulnerable but it will be worth it if its the right guy.

Stop paying and stay in!