Divorced and dating again; how do I do it?

Hey Guys,

I am back in the dating game after being married for twenty years. (I’ve also been single and alone for the last two after the divorce.) I finally decided to try online dating and I met a woman who I like. I’ve been seeing her for a month or so. Things are starting to progress I think. We’ve been going to the movies and hanging out but I’m kind of struggling to come up with cool date ideas. What do you suggest?


Dear Mark,

Thanks for your question. We can see how the prospect of dating after twenty years of marriage might be daunting. You last dated in the era of grunge, mood rings, Will Smith, scrunchies, Backstreet Boys, and Pulp Fiction. The world’s changed a lot since then, but dating hasn’t really. A woman still wants the same essential things. She wants a guy who listens, makes her laugh, takes her out, converses with her, gives her gifts occasionally, and respects her and loves her. Those would be the most important things to focus on with your recent foray into the dating world.

We’re happy to provide you with some basic date ideas but we’re sure you’ve got some creative juices running through your body. Probably the more you do it, the more ideas will come to you.

Here are the real basics that every guy should know:  

1. Dinner: Find out what she likes and keep it simple. Pick her up. Push her chair in for her. But let her order her own food. And then sit back and have a nice conversation. Don’t forget to chew with your mouth closed and don’t have food in your teeth. Seriously. It’s easy to forget. Don’t drink too much where she’s concerned about you driving her home.

2. A walk: Yes, dates during the day can be fun. Some exercise and good conversation are a potent combination. The venue is up to you. A park is always nice, but so is a nice neighborhood.

3. Take a trip to the city or the country: Depending on if you’re a city mouse or a country mouse a trip to the opposite place is a nice change. If you live in the busy confines of the city, take her out for a drive in the country.  Sip some coffee or cider with the windows down and the radio on. Keep it quiet enough for the two of you to talk. If you live in the country, there’s nothing like a trip to the city to take in a show, or have dinner, or just to walk around. Maybe even take the train because parking will be a pain.

4. Go to a game. Yes, that’s right. She may not be into sports but it will be fun. Baseball, basketball, hockey or whatever. Any of these will provide you with a festive atmosphere to cheer, get rowdy, and bond. There may even be some moments of snuggling, especially during a boring night game when the home team’s getting crushed.

5. Take a class together: There are a ton of adult ed classes the two of you could take together. Cooking, yoga, French, maybe even Tantric Sex. (Just kidding…..kind of.) Anyway, what better way to get to know one another then by learning something new together.

6. There are many more elaborate ideas, but we leave that up to you. You can do it!

Does this help?

The last bit of advice we can give you is to be yourself. If you don’t have a lot of cash don’t try to be a big spender. If you don’t like wild and crazy then don’t take her out to a wild and crazy place. You want her to dig you for you, not for the guy you’re pretending to be. Authenticity is still a huge part of the dating game.

And there you have it. Let us know if we can answer any more of your questions. And good luck.


Read More: Relationship Advice and Dating Advice about Dating with Kids or Dating after Divorce.





40 Comments on Divorced and dating again; how do I do it?

  1. hey guys. how do i get a get to step up, i went on a date and hes really interested, met up with me and then after the date ask me for another day, which we planned then he canceled on me but the rearranged it, for tonight but hasnt brought it up yet. he’s still texting me saying how much he likes me and finds me very sexy etc, glad we have so much in common. but it seems a little like hes relaxed alot from our fist date, how do i get him to see im not gonna be one of those women thats happy to be let down and he needs to step up? thanks you b

  2. @Bex…….You show him by ignoring him if he does it more than once. You don’t want to get involved with the kind of guy who doesn’t get it.

  3. Is he still sleeping with his ex? // February 28, 2013 at 1:29 pm //

    I’ve been dating this guy for a bit. we knew each other years before, and he was renting an apartment with his girlfriend at the time. they moved into a house together, and have since broken up(or so he says). they still sleep in the same bed, although he says they don’t touch each other. the reason i started dating him was because while he was lliving with her in the rented apartment, he never made a move on me, even though there was chemistry. He says he would never cheat, but he’s not making as much time for me as he did in the beginning, and he is constantly going to strip clubs and bars with his “buddies” spending weekends away. Im worried that he is having his fun with me and going back to his girl of 9 years. Am i being jealous/insecure or is this a bad situation just waiting to get worse?

  4. @is he still sleeping with his ex…….Seriously? You already know the answer to your own questions. He still sleeps in the same bed with his ex? He goes to strip clubs and bars all of the time? Weekends away? When do you actually get to see him? This is going to get worse. And you’re going to regret it.

  5. @Theguys- hey there i had a question but couldnt find the closet questions asked close to my situation so here goes it- i met this guy threw a friend we have been talking just a month.. Everything was going really well.. We talked all day and night everyday all day, hung out, went on some dayes.. Told me how much he adored me and how happy he was to meet me.. Then suddnely he started to not be as cherry when talking to me and not bothering me with as much. I kept asking why and he kept saying he was just busy with work.. Then finally i got it out if him he just wants to go slower and be friends first which i understand because we wherent really friends first so i agreed to go slower and get to know eachother.. He also said i still really like you and still want to talk all the time ect.. And everything was cool being friends Then randomly starts ignoring me or one wording me. And saying hes just busy? What do u think went wrong?

  6. @Ariel……Most likely he was never completely sure how he felt about you and finally decided he wanted to be friends. There could also be another woman you’re not aware of. Don’t bum out too much. Move on and be open to the next guy. This guy isn’t the guy for you.

  7. I haven’t dated in 3 years & have never been good with guys really. I ended up meeting a guy who has been facebook friends with me for sometime now. (We are in the same line of work.) I noticed he spotted me and did a double take. Towards the end of the night I he ended up finding me talking with other business associates came over and introduced himself. I have to admit I was flustered lol that NEVER happens. He kept looking at me while i was talking to others in the group he asked me questions about myself and smiling. He wanted to know if i was going to the after party I said no i’ve got to hit the gym in the morning. He then leaned in to show me something. I did flirt back with him a little. I said it was nice to finally meet you and i’m sure i’ll see your face around with a smile he gave me a hug before he left. How do i tell if he is interested in getting to know me more or if he is even interested in me outside of friendship? he still follows me on facebook and comments. we go to the same events ever 3-4 months. Is there something i can do to let him know i’m interested without being to aggressive since i want him to pursue me? Thank you for your help guys!

  8. @Brooke…..When did you actually meet this guy? How long ago? In general, it would be good if he pursued you.

  9. Brooke // May 3, 2013 at 1:16 pm //

    i met him probably 2 or 3 weeks ago

  10. @Brooke….well, that helps. Definitely let him pursue you. It’s hardly been any time at all. We know it’s hard, but be patient. Good luck.

  11. arianna // May 6, 2013 at 7:06 pm //

    Hi im a freshman in highschool and im so confused about my crush.
    He told me he’d pursue a relationship with me after we had sex.I know what you’re thinking don’t do it.I know and i don’t want too. Im not ready for all that and my parents would kill me if i did something stupid like that. He says we can “talk” after we have sex and i also haven’t had my first kiss and I kinda wanted him to give me it but he says ” ill give you it while were having sex”

    Whats wrong with this boy?! I like him a lot but I honestly don’t think he deserves my virginity. He’s also my age and isn’t a virgin. I’ve tried and tried reasoning with him even asking if he would wait until i was 16 and he said no. I told him the risk of having sex (like getting pregnant) and he ignored me. I will have to deal with him at school next year and i know that its not going to be easy to stop liking him cause I’ve liked him for so long. What should I do? P.S. He says he likes me too and that im the only girl he wants to do this with.

  12. arianna // May 6, 2013 at 7:08 pm //

    Hey Hi im a freshman in highschool and im so confused about my crush.
    He told me he’d pursue a relationship with me after we had sex.I know what you’re thinking don’t do it.I know and i don’t want too. Im not ready for all that and my parents would kill me if i did something stupid like that. He says we can “talk” after we have sex and i also haven’t had my first kiss and I kinda wanted him to give me it but he says ” ill give you it while were having sex”

    Whats wrong with this boy?! I like him a lot but I honestly don’t think he deserves my virginity. He’s also my age and isn’t a virgin. I’ve tried and tried reasoning with him even asking if he would wait until i was 16 and he said no. I told him the risk of having sex (like getting pregnant) and he ignored me. I will have to deal with him at school next year and i know that its not going to be easy to stop liking him cause I’ve liked him for so long. What should I do? P.S. He says he likes me too and that im the only girl he wants to do this with.

  13. @Arianna……Well, if you knew what we were going to say then why did you ask. DON’T DO IT!!!! Seriously. It’s a very bad idea. This guy is a manipulator and a player. But we’ll give him one thing. At least he’s being honest with you and telling you he wants sex from you. But he shouldn’t be promising a relationship. That’s what bothers us. Listen Arianna. You’re too young. This is not the right time and this is not the right boy. Think about this. Let’s say you have sex with them. And then let’s say the two of you go out for a little bit but then break up. How are you going to feel then? Probably very upset and angry. You’re going to feel used. And then you’re going to be mad at yourself. And lastly. If you’re that unsure about this, that should tell you all you need to know. Trust your gut. It’s telling you something is amiss. It is. Time to move on from this boy and find a good guy who’s going to treat you with respect.

  14. Hey guys…i’m in a real fix this time..
    Okay, i’m dating this guy for about two months.
    We’ve been friends for around two years before that. He proposed to me, and since i always thought he understands me really well,I was more than happy to have someone.
    Now, I am not the forward types. Not at all. Iv got some principles set up for mysself, and i dont believe in stooping down to please anyone..which includes that i do not want anything physical with him unless and until i’m a certain age. Cause i already have too much to handle in life.
    And with him, its like he doesnt belive in setting up any limits for himself and believes in being happy in his life. Although i always made this clear to him…once when we were out on a date, he did kiss me. Assuming that he would have control on his mind, i didn’t mind the kiss. Later, we would speak on the phone at nights and he would want to jerk off while im talking to him..and he would even speak about sex with me. I kept making it clear that we would never go ahead of kissing or make outs.
    But, he still does come up with sex and whenever we get into a romantic mood, it has to be dirty..
    Even though we have a lot of similarities, we totally differ in what we want from this relationship…and i will never be able to give him what he wants..not until its the right time.Although he does try to keep me happy and hes understanding.
    I am in a fix, cause this keeps scaring me..and i obviously do not want to do anything that harms my self esteem.
    Please help me with what i should do to make him understand..or will this relationship work..?

  15. @Anu…..So how old are you? And at what age do you want to be physical? The bottom line: Don’t do anything you’re NOT comfortable with. He seems to have sex on his mind. That should give you a good idea what he’s after. Do the two of you ever do anything together? Like go out to dinner, movies, dancing? Have you met his family? Friends?

  16. I’m 20 and hes 20 as well.
    We study in the same college together…and we are in the same class.
    We have mutual friends and I hav met his family once. He is from a different city so I do not know his old friends…but those from this city,i know..
    Yes…we do go for movies and lunch dates…and meet up for sometime whenever possible, cause it feels good to have him to talk to and share..
    I dont hv anything physical in mind until im married and old enough to make the right decision for myself..
    Well, I have brought this up to him, and he tells me that the relationship is far more important to him than any physical intimacy..but then i’m not sure if a guy who has sex on his mind can actually leave his fantasies for a girl who doean’t

  17. I’m 20 and hes 20 as well.
    We study in the same college together…and we are in the same class.
    We have mutual friends and I hav met his family once. He is from a different city so I do not know his old friends…but those from this city,i know..
    Yes…we do go for movies and lunch dates…and meet up for sometime whenever possible, cause it feels good to have him to talk to and share..
    I dont hv anything physical in mind until im married and old enough to make the right decision for myself..wont be before i’m 25 atleast..
    Well, I have brought this up to him, and he tells me that the relationship is far more important him than any physical intimacy..but then i’m ot sure if a guy who has sex on his mind can actually leave his fantasies for a girl who doesntt even think like him..
    A lot of times when he brings up sex even while talking in general..i start to feel like I dont share that much of an interest and I divert the conversation, thinking that by talking with him about this ,i’ll only end up giving him some wrong ideas..
    Is this the correct way to go about it?

  18. @Anu…….You’re just going to have to wait and see. But understand that sex will always be on a guy’s mind in the company of an attractive woman. That’s not necessarily a bad thing. But if he doesn’t eventually ask you to be his girlfriend, then it’s unlikely he wants more.

  19. Hi guys, thanks for a great site, it’s really informative as well as entertaining. I want to ask you your opinion about something that has been puzzling me. I’ve been with my boyfriend for just over a month. I’m 21 and he’s 23. Things got quite serious, quite fast. We had already said ‘I love you’ by week three, I met his parents a week after we started dating and we’ve booked a vacation together for this summer. Now he’s started talking about babies a lot, what we should name our children (he’s got a few names picked out), where we should live, where we should get married etc. I can’t figure out if he really means it or if it is just for fun. What do you guys think? Is it normal for a guy to start talking about children after only a month (well I guess it’s not normal but what could be the cause)? I live in a country where people usually don’t have children until well into their 30’s so this is not a cultural thing. Another thing, if he is indeed serious, as I worry he might be, could it be that I’m doing something wrong? Sending some sort of ‘settle down with me’ signals? My last relationship ended when the guy proposed after only four months and i turned him down, I was 19 at the time. Well I guess this is it, I’m sorry to ramble on like that. Thank you guys, hope you can help me with this! 🙂

  20. @Hannah……It sounds nice, so try to enjoy it. But you have a right to be questioning things. He’s moving very fast. And we can see three reasons he might do this: 1. He thinks you’re so hot and amazing that he’s worried a lot of other guys will be after you, so he’s trying to stake his claim and make sure he has you sewn up. 2. He’s the kind of person who loves the idea of love and so this is something he does. 3. He genuinely thinks you’re amazing. …….Obviously the third option would be best, that is, if you feel the same way. But generally we think this is pretty fast. You’re in the honeymoon phase still. And for a guy, that means he’s in the perpetually horny phase, which means he’s completely infatuated with everything you do. Let’s see how he feels in six months or a year. Enjoy this, but keep those eyes open. The longer it goes, the more answers you’ll have.

  21. Hi guys, sorry for a long post, here is my dilemma. 7-8 months ago I met this guy I felt attracted to from the first minute even though he isn’t even my type, plus there is way too much reasons I should not like him. I was slightly flirty , he was too ( or maybe he was just generally flirty/ friendly and I saw what I wanted to see) so I was even considering rethinking the reasoning based on wich i should have stayed away from him. But very soon he got into a relationship / fling with someone else, which didn’t last long. After that there was another short term fling with another girl. Through out this period we were kind of afriends, I kind of ignored my attraction and was friend with him since he is a great person to be around with, charismatic, positive, encouraging etc. all was good I was more or less over him, but about 3-4 months ago he became kind of aggressive towards the guys I would potentially date, explaining this with some lame excuses, I ignored his behavior and he stopped. Soon after that he broke up with this second girl ( don’t have an illusion that it was for me) and changed towards me, became more flirty(unless I’m imaging that) for the last 2-3 months we both have been really flirty to each other: long eye contacts , “accidental” touches , just looking at each other and smiling like stupid without reason, most of the time he is overly protective and caring , usually notices very little details about me and used every opportunity to be around, overly I feel there is a very strong mutual physical attraction between us ( hopefully that’s not only in my imagination) but on the other hand he have not proceeded, even though I think i made it pretty clear that I’m interested too and would be open to his advances, besides most of the time he is amazing but ones in a while he is very cold , sometimes even ignores me completely. So I’m really confused is he really like me or just being friendly? Another detail, he always had some nicknames for me but recently started calling “little girl” , yes he is physically bigger than me and 7-8 years older but come on I’m not a kid , I’m in my mid 20s. Sometimes I assume that maybe he looks at me as a younger friend, but than he checks me up
    The way I’m pretty sure guys don’t check out just friends. Also recently he started offering help about something I have not asked for and I don’t need and then forgets ( or pretends to forget) to do it. Why the hell he promises something he knows he won’t do it? So I would really use your suggestion what to think about his behavior or what to do? He completely messed up my head, stopped seeing this for me perfect guy whom I recently met and don’t care about anyone else . I see him almost every other day and spent the rest of the time waiting to see him, hardly focus on anything else, tried few times to stay away from him since it doesn’t look to go anywhere and even if it goes not sure if its a good idea, but every time he does something irresistibly cute and I forget that I was upset on him right away , is he playing me? Thanks, Nikki

  22. @Nikki…..yes, he’s playing you. And it’s working. He’s got inside your head. That’s the first step to getting in other places. (IF you catch our drift.) Of course the age difference could be holding him back too. But still, he’s had his chances with you. He knows whats up. He instead chose to date two other women, and not pursue you. We don’t see this going anywhere. Sure, you could fall into a sexual relationship with him for awhile, but we don’t see long term potential. Why? Because he doesn’t see long-term potential. Otherwise the two of you would already be going out.

  23. Thanks guys for feedback. Haha, I caught your drift and sadly for me, your opinion exactly matches to my thoughts generated by few of still “uninflected” cells of my brain. By his actions he managed to make me pursue him. Damn it, I know what he is doing and can’t still stop it. But on the other hand there is a voice inside my head telling me that maybe he doesn’t know what’s up and if I’m really interested, or he is shy and that’s why he is holding back (though didn’t look shy with those other girls) if he is playing why he started being and still stays friends with me and didn’t use the same “fast track” technique he successfully used previously? Just because he knew it would not work and it has nothing to do with him genuinely being interested in me?

  24. @Nikki……You’re just going to have to trust your gut on this one. It’s hard for us to say. We stand by our original feedback, but hey, it’s possible we could be wrong. Just keep your eyes open as you move forward. Good luck and keep us posted.

  25. VicariousVillain // June 19, 2013 at 9:25 pm //

    Hey guys,
    I broke off my engagement about a month ago, for a long list of reasons. The short of it is that she wasn’t the person I thought she was. I knew it was over, so I got over the whole thing in no time. There’s another girl though, I’ve been friends with for almost as long as I dated my ex. This girl and I have had an admitted mutual attraction since the day we met, but we have both always been in relationships.
    Now, we are suddenly both single, and want to give it a try. Great! But I don’t want to look like an A-hole to my family and friends, as I jump back on the bandwagon a month after my un-engagement.
    So is it too soon? Should I let this one go? (She’s an amazing catch, I’d hate to miss out on what could be something wonderful)

  26. @Vicarious Villain…….Can’t you get to know her without jumping right back into something serious? Meaning, spend some time with her and maybe explain to her where you’re at and see how it goes. Start off as friends. And honestly, you might be attracted to this woman but it might be a bit too soon for you. Are you really emotionally ready for something new? We’d hate to see someone you think has some serious potential turn into a rebound because you’re not really ready. As far as your family: Hey, you’ve got to live your own life. Just try to be a bit subtle and it will work out. Good luck.

  27. I just want to know if I am overthinking this or not. This is regarding my best friend’s new roommate, we’ll call him Roger. I see and spend time with Roger a lot only because I am always at their place after work/school and I have gone on roadtrips with them and other friends. However, we don’t communicate outside of these interactions. He is naturally flirtatious to any woman he meets, so its not unusual for him to dish out compliments on a woman whether she is a friend or love interest. He is a little younger than me and a total player so I don’t really take him seriously. But lately he has been acting interesting. One weekend, we had a bbq at their place with a bunch of people in their apt bldg, I ended up meeting a new guy that night. This new guy caught my attention because he was strangely more quiet than everyone there that night, but he and I talked a lot that night (good convo), he doesn’t drink or smoke, he is really handsome, and we ended up trading numbers. At the end of the night, my bestie, Roger and I were talking about the night, and Roger kept saying he thinks the new guy I met is gay. This new guy is definitely not gay and everyone else who has met him doesn’t think so either, so I think its funny Roger keeps saying this. Then last weekend we all went clubbing together for a friend’s birthday. I must say we all got pretty drunk and were dancing all night on the dance floor. Usually when we go out, Roger does his own thing and dances with all different girls in the club, but never with me or my friend. But that night he grabbed me to dance and we ended up dancing a lot. He even ended up giving me a crazy lap dance in the club. I ended up spending the night at their place that night and when we walked into their apt, he kept bumping into me and then lightly slapped my butt. I just told him you need to go to sleep cause I knew we were all drunk. I ended up collapsing on my friend’s bed, while she went to the bathroom. While I was laying there, Roger came in a laid on top of me and sort of cuddled me and mumbled how drunk he was. I didn’t cuddle him back but I didn’t force him off either. It only lasted for like 10 sec and he got off as soon as he heard my friend coming in the room. The next morning he said he didn’t remember anything from last night (nothing about the club, how we got home, like nothing). He said he was so drunk. My bestie had to remind him how much he danced with me and he was like “Oh yeah cause Mary can really dance”. The only reason I think he is lying about not remembering the previous night, is because later on that day he says “Oh yeah Mary was a mac daddy last night”, which was sort of true because I danced with a lot of guys and more than a few guys were trying to get my number 😉 But if he supposedly was soooo messed up that he couldn’t remember anything how could he remember that? My verdict is that this guy is starting to crush on me. And I guess I want to know cause I sort of have been secretly crushing on him too. What do you guys think? I don’t think I would do anything about it anyways because he is my bestie’s roommate and he has proven himself to be a major player. Plus he doesn’t contact me outside of when we see or hangout with eachother. But when we do hang out we have a lot of fun and talk….what do you think?

  28. Dumbfounded // July 17, 2013 at 11:16 am //

    Hi guys. A few years ago, I reconnected with my first love after many years (having both been previously married). The love was just as amazing as it had ever been. He was all in but, for various reasons, I wasn’t on the fast track (i.e. living together within 1 month) that he was. I also felt like I only had a piece of his heart, as he had/has what I felt was a co-dependent relationship with his daughter, ex-wife and in-laws (basically still acting like a family unit). Ultimately, I had to relocate. It crushed him. We tried to make it work long distance but the short story is that it didn’t. Yet, there was no real closure and the love was/is still there. I started dating someone else. He started dating someone else. I am now living back in our hometown and single. He is still in a relationship. All along, he has maintained that we would end up together down the road, that he still had feelings for me, etc. At a certain point, I made it clear to him that I was hopelessly in love with him and, despite trying to let him go, still held out the dream of marrying him one day. When I first arrived back home, he said he felt that his relationship with his girlfriend was over. He came over. We slept together. (This is a guy who never was a cheater – not on his ex-wife or me.) Since that time, he’s been back and forth about whether their relationship is over. He continues to text me, often as if we are still a couple. If he’s been drinking (also something he didn’t do much until recently), he will be even more forward. Recently, he asked for nude pics/video. He did not get any. Instead, I told him that I had made the decision to move on. Part of my problem is that I have always believed (and in the past have been successful) that old lovers can be friends. But, I see that, in this case, it may be too difficult. I also feel like I don’t even recognize the man he has become. I guess I’m just looking for some insights from a guy’s perspective so that I can get my own internal closure and truly move on.

  29. @Dumbfounded……The real question is: Do you really want to move on? If you don’t, then you’re going to have to hang on and see what happens. It’s obvious he’s torn about what to do. He’s probably not jumping back in with you because he doesn’t trust that your feelings are for real. He doesn’t want to get left in the dust again. And you can see why he might feel that way. Why don’t you have a heart-to-heart with him and tell him what you really want. Because……We’re just wondering what happens if you move on, but then he breaks up with his girlfriend a year from now. What are you going to do then? If you’re going to move on, move on. But if you’re not ready to do that, do everything you can to see if you can make this happen. If it doesn’t work out, or he turns out to be someone you don’t want to be with, then at least you’ll know you did everything you could. You’ll get the closure you need.

  30. Hi, i actually wrote this on a different oage but I hadn’t gotten a reply for a while. Anyways I’m confused about whether or not I should pursue a relationship with my neighbor. Im 17 and I’ve know him for an very very long time.He two years older then me. See we actually grew up together but not in the way where we became good friends. We used to play a lot with his cousin and my brother but you know little boys rather play with other boys than girls, so I was the odd one out usually. Eventually we stopped playing together because my brother and I had a strict “babysitter” who wouldn’t let us leave the house to play. So after that we all just stopped talking. (I actually had developed a little crush on him when we were younger)Well now I’m older and have A LOT more freedom then before but I still haven’t had a boyfriend because I’m really shy around guys that I like or don’t know well.(Towards him it the combination of both) He’s always polite to me and (when I get the courage) he’s really nice to talk too, but I can also see that he’s shy. I’ve had this habit of looking into people eyes when I talk to them. (this has gotten mixed reactions from people) I asked my friends about it an they all say it used to creep them out/make them feel weird so they try not to look, I had already noticed it though lol. Normally I would just think he’s looking away because of that but the first thing he does is smile and say “hello” and look away. (Faster then most people) My friend has also said that she seen him checking me out. So far his Dad and Grandmother seem to be trying to push us into relationship. His Father actually said that I should hang out with him, and considering our ages I don’t really think its for a friendship. With his family “encouraging” me to hang out with him its adding on to more of my concerns… I don’t know if it because they’ve noticed a change in him when I’m around/he’s talked about me, or if it just because they trust me since I’m very nice/ they known me for so long. I’m not really concerned with our age but, after summer, I’m going to be a senior in high school. What if I do get into a relationship with him? It’s very likely that I will be going away to college out of state. Is it too late to bother trying to be in a relationship? And the biggest question: How would I even go about asking him out? He’s my neighbor, it makes it so much harder for me because I’d be super embarrassed if he said yes or no (more so if he said no). He doesn’t look like he’d make the first move and plus I’m not sure if he’d even want to because his family seems so interested in me. =/

  31. Dumbfounded // July 21, 2013 at 11:25 am //

    Thanks Guys. I appreciate your feedback. There was so much more that I could have written but I wanted to keep it short for a variety of reasons. I actually did have that heart-to-heart with him and told him what I wanted – him. I actually have done this 2 or 3 times. He has affirmed that he knows where I stand – that I have made it clear. He also doesn’t act like he doesn’t believe me…though he does acknowledge not wanting to be hurt again. Yes – he has said that he is confused…and that confusion continues to drive a wedge between us. But, I do see why he’d be afraid…and, though I’ve tried to address that, I appreciate your feedback and perspective. In a round about way, it does give the closure that I need…as this has gone on now for close to a year. Thanks again! I appreciate the work you are doing here!

  32. @Alisa……Let him be the one to initiate. If he’s not mature enough to do it, then he’s mature enough to date you. Keep us posted and good luck.

  33. Hi, Guys. I was married for 11 years, 35 and is now a recent divorcee. I have a 6 yr old son, and 2 teenage daughters who live out of state with their father. I’am not up-to-date on the protocol of dating. Gosh, I don’t even know how to ask you guys questions without scratching my head. I am dating 2 men casually. One guy (lets call him Rob), divorced, 35, 2 young teenage kids, lives in the same town as I, and the other (lets call him Paul), 39, no kids, never married, lives 2 hours away. I met Paul about 2 months ago. We have gone on 4 dates. He took me out to dinner and showed me his hometown. I slept with him once. A really nice guy and when he calls or we are together, we have deep conversations, but he rarely asked questions about me. He barely calls or texts, but when he says he’s going to call, he does. He only texts when he wants to plan a date or he’s sharing something that happened to him or asks how my day is going, but he does this rarely. Usually it takes him a while to text back even when he’s the one initiating. Everything about him from the beginning to now is consistent, as far as his communication. About 3 weeks ago, I met Rob. He initiated all 4 dates. He took me out to dinner, movie, walks in the park with ice cream, and showed me areas in this town that I haven’t seen, since I am still new to this town. He texts me everyday to share what he’s doing, his plans, or asks me what I am doing or what my plans are for the day or night. He shares with me about his future plans as far as his activities with his son, just in case, I want him to take me on different hiking trails (which he offered), or hang out with him. When he picks me up on dates, he always opens the car door, and he pays for everything. He’s still doing all of this, even though I had already had sex with him. I am attractive to both of them. I really liked Paul in the beginning, but now that I am dating Rob, I like him more, because he shares so much of his life with me and he asks me about my family, kids, my ex, and my likes and dislikes. My questions are…Can a woman initiate a text or wait for the guy to initiate all communication because a guy told me once that “its 2013” when I told him a woman shouldn’t be the first to text? How can you tell when a man is genuine or just being nice because he has ulterior motive? Is it okay to date 2 guys at the same time? Because I rather be kissing one frog, rather than 2. Would greatly appreciate your feedback. I told all my single and married friends about your site. Your site is fantastic!

  34. @Syd…..It’s okay to date two guys as long as you’re honest with both of them. Actually, you don’t need to say much initially, but if you’re really starting to date them more regularly—especially Rob—he need to know about Paul. It’s only fair. From our perspective, Rob seems like a better match. He certainly seems to care more about you. Paul sounds like he contacts you when he’s bored or wants sex.

  35. @One of The Guys. A breath of fresh air! Thank you so much for your input.

  36. @Syd….You’re welcome.

  37. So I have known this guy for several months, just as friends..I always thought he was hot cause he was a cop. One night he messages me on Facebook an we got to talking and it was purely a hookup and I was fine with that…well we kept seeing each other a few times after that. He would always give me a hug afterwards as I was leaving, everything was fine and dandy. It got to where I was having to text him. He would always respond immediately. it was a few days before my birthday and I said something about “birthday sex” well I was suppose to come over there that night but he said that he was going to his mothers house and should be back later….well he textes me about 3:30am and ask me if I was still out, I wasn’t so I didn’t reply til the next morning. Well I don’t hear nothing from him so I texted him one more time…he texted back, evening darling, and never got a response back when I replied…so this was Sunday and I had not heard nothin from him so I texted him and said look if you don’t wanna hook up anymore then all you have to say is your not interested. He said hell no, he still did wanna hook up. He had had his little boy. I said ok well that is understandable we got to talking. Well anyway he told me to hollar at him the next day and I did. Never got a response, well I was texting my friend about getting a steroid shot in my butt lol as I accidentally texted to him. Well of course something perverted came out of his mouth and I asked him if he still wanted me to come over? Never got a response. So I got to thinking, I asked him a random question(nothing sexual) and about an hour later he texted me back??? Then we just got to talking about him and if he was excited about starting work back cause he was injured. Well Tuesday, and Wednesday he would talk to me but avoided the question but would talk about anything else. So we were going to hook up Thursday but I was busy so we decided on today (Friday). I texted him Thursday to see if we were still on and never got a response and I texted him this morning and never got a response. Also…the last time we hooked up he scratched my back and he said well I hope your boyfriend does not mind. I am pretty sure he knows I do not have a boyfriend…cause I have told him. I need help cause I am confused. I am fine being FWB but I don’t wanna seem to clingy by asking if he wants to hook up. And I keep getting mixed signals.

  38. @JD….You’re not getting mixed signals. He thinks of you as a booty call. So when he’s horny for you he responds and acts all nice. When he’s not, he’s distant and doesn’t return your texts. Clearly he has several other women he’s treating the same way. Honestly, we’d avoid this whole situation. It’s only going to get more and more confusing. In fact, we’d avoid all hook ups and booty calls in the future. But that’s just us.

  39. Hi again, I am seriously confused about my neighbor. He asked me out about two weeks ago, but he said that he would be busy with school for awhile. I agreed to going out ehen he had time, I didn’t give him my number at the time bc I was surprised when he asked. He hadn’t brought up not having my num so I ended up having to and gave it to him. That was almost a week ago. I thought he was interested in me, but he never texted or called. What was the point of asking if I wanted to hangout if he wasn’t going use my number?

  40. Okay, I don’t know whether a should tell my boyfriend about this because I know this will cause some problem. Today someone knocked at my door and as I opened it, I realize it was one of my boyfriend friend. Which he’s married to my boyfriend cousin. So he asked for my bf n told him he was at work, so he just went straight ahead and told me that he liked me and wanted my number. I was in shocked, like wtf. I was like no I can’t give you my number and I have nothing to say about that. The thing is that I don’t know if I should tell my bf about it. Cause I know maybe it will destroy their friendship and maybe the guys marriage. Or should I just stay quiet and forget about it.

Leave a comment

Your email address will not be published.

Maximum comment length is 1500 characters.