Your question was: Low Budget dating (online dating with Match.com) - Again?? Need Input.

I dont think you are being unreasonable by trying to think of different ways to spend time under $20.  There are many concerts, lectures, $1 movie theaters, art exhibits that the two of you can do together.  You can say something to him about how there are many things to do that wouldnt cost you guys much money and you would rather be out in the fresh air walking than sitting indoors.  You can also add that you dont feel you are at the stage in your relationship (thru Match.com) where it is appropriate to spend too much time alone indoors.  Good luck!..

You know I like your words "would rather be out in the fresh air walking than indoors at home".  I will use that when we talk tomorrow. .

Dating does not get any easier - I am 46 and he is probably 60 or close to it.  I think also the fact that we have been buddies for so long adds to the pressure of making sure we are careful about what we do plus we both dance and socialize in the same circles...

I am 45 and I hope to reenter the dating (online dating with Match.com) world sooner than later.  I have never enjoyed the dating (online dating with Match.com) process.  I just have some personal issues that need to be dealt with and put to rest.  I cant believe that you are dealing with a 60 year old that has to worry about these things.  Scary, isnt it?  It is smart that you think these things through since you socialize in the same circles...

After my experiences with men I decided that if a guy is in worst financial position than myself, then there is a very strong reason: addiction, bad choices, irresponsability, mental/emotional issues etc. and that I need to just keep moving.  I was a single parent supporting my kid with no help from my ex-husband and if I got myself together after that horrible marriage, than a man should be able to do even better than me..

Bob is a nice guy, got screwed by two ex-wives. I think something "broke" inside.  He was "someone" and now well, he is not.  He is now older and I know very well how hard it is to find work after 50 (I work in the employment industry).  So I am trying to keep open minded and like someone said to me "it is just a date, lighten up a bit".

Yes, I think it is important for us to work on our "stuff" before we bring someone else into the mix. I did not date using Match.com for 11 years because I needed to work on myself and not have any distractions. ..

I think your instincts to not let him hang out at your apartment are very good. I know what you mean about your apartment being your sanctuary. In my last relationship (thru Match.com) I allowed the man into my apartment on the third date, even though it didn't feel right to me, and somehow I ended up feeling the whole relationship (thru Match.com) was rushed. Maybe I never really got a chance to catch my breath after that. Taking your time is the way to go!.

As far as the finances, I too have found that when a man has serious financial issues there are often emotional/psychological issues as well. Proceeding with caution is a good idea.

That said, I agree that there are so many things you can do very cheaply on a date using Match.com and you can have a really good time. Just taking a long walk can be really nice..

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Thank you, thank you Stephanie for your reply.  I always need to double check my thinking because I am very well aware that because of my past experiences I am sometimes extra sensitive to certain things and might - at times over react to them. Like men who are financially unstable..

Hmmm, I did not think about the "rushing" aspect.  I know Bob has liked me for 10 years....but 10 years ago I was having way too much fun and I was not thinking about relationships and dating (online dating with Match.com) and settling down.  I was having the time of my life! Which was good - I needed it.  It helped to clear some of the bad memories and give me confidence and practice dealing with men in general.  Now, I am tired of the superficial and I am looking for a relationship (thru Match.com) and maybe not get married again , but a boyfriend. I am now wondering if he is trying to "rush" things - he has been trying for 10 years to get me to go out with him and finally I said "yes" to going out with him two weeks ago.  Interesting point.  .

Thanks again - I appreciated your insight..

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He doesnt appear to be rushing things, based on what you posted.  Guys dont think anything of it to go to a woman's house and watch a movie and do a little necking.  After you have been married and divorced, and having the availability of a person right there to do those things with...it is very hard to go back into the "dance" of dating (online dating with Match.com) again with all of the rules and etiquette issues...

Well...I kind of want the "dance" part since I have not really dated that much.  A lot of flirting and kidding around but very little real dating (online dating with Match.com) experience.  Once it is real, then things seem different than when you are just kidding around..

Funny that you say "dance" because I have been his dance buddie for several years and for a few events I was his official dance partner..

Well see how official date using Match.com #2 goes. ..

I think that you go out your way to "accommodate" your cheap dates,  you don't have any boundaries and that's why you end up paying for both of you AND feeling resentful and mad. GF aren't banks and loaning money to BFs is the worst mistake that a woman could make ever in a relationship. Men know it and if the man asks for money to his GF then he's not an individual who fully sees her as a partner. He sees her as a way to get by. Men can ask their buddies, parents or bosses for money in a time or need, OR they can go work for a few hours to get a few dollars.

If this fellow guy cannot afford to pay for a "bite to eat" date using Match.com and rather wants to share his bowl of soup with you then let him. Ask for a second bowl for yourself. Don't offer to pay for your food, not even at a McDonald's.  Set up boundaries for what you'd allow a date using Match.com to do or not.

If you can stand this situation then keep on dating (online dating with Match.com) the broke guy, If no then move on to another one.  As for watching DVD's at your place you should set up boundaries from now on. You don't yet feel comfy having him over so he better think of another thing to do: walk down town and go window shopping, go to the mall and have an ice cream cone while chatting at the food court, go to a free museum, etc. There is stuff to do, the thing is that this guy seems not to be motivated enough to search for stuff to do...