Online dating: Should I move forward?

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Hi Guys,

I am 37 and a mother of 2 kids. I have tried online dating which I am not so comfortable with.  Nonetheless, I tried it and have exchanged messages with different people from different parts of the world, but all just short notes. One time I received several nudges and winks from a guy with no profile picture.

For no reason at all, I decided to write and send a note. He sent me a message and we started chatting. Fortunately, the guy is extremely gorgeous and a real nice guy. He has showed sweetness and interest in me but on other days, I don’t feel it.  We’ve been chatting day and night for about a month now. Sending messages and talking on the phone. He is in Canada and I am in Asia. He does say that he will come here, but he doesn’t really tell me the purpose of meeting me. He says he will come to my country (he really adores women in our country) grab a girl and marry her, but of course the chemistry should be present.  He’s 38 and I am 37, and he said he want someone younger because he still wants to have kids. So this is really confusing me. I do like him. We do have chemistry; we enjoy our talks, we have something in common, we believe in the same things—morals, values—but it’s really puzzling me.  I don’t want to fall in love. We have not met which is crazy but I guess I really like how he is—not just the looks.

Should I stop?  or should I just go with the flow?  Should I show I am interested in him?  We do call each other with different words of endearment but that’s about it.  He never said he likes me, but he would always say I’m pretty and he seems happy whenever we talk.  Please, I need a guy’s perspective on this.


Single Mom

Dear Single Mom,

Thanks for your question.

While online dating has become very common, and in some cases successful, it’s still the wild frontier, especially in your situation where the two of you live in different countries. We would tread slowly and carefully with this person.

The first red flag is he doesn’t have his picture up with his profile. You say he showed you one after you started chatting, but you do realize he could have shown you a picture of anyone and you wouldn’t have known the difference? That’s not to say it isn’t a picture of him, just that the possibility is there that it’s not.

He’s also said he wants someone younger so he can have his own kids. Has he said anything about your age, or the fact that you already have two kids? Is he interested in taking on the responsibility of being a step-father? You need to have a much more in-depth conversation about this topic. Our sense is he wants someone even younger without kids.

We think you’ve got a lot of talking to do if you’re really going to be serious with this person. You need to find out more about who he is. What are his previous relationships? What does he do for work? Does he have friends? What’s his family like? What are his interests? Where does he stand on religion, politics, etc.? Then, you need to discuss the bigger topics like what you both are looking for in a partner.

We know it’s exciting to start talking with someone new, especially if you’re attracted to them. (At least the picture he showed you.) But at some point you’ll have to actually meet him, and get to know him on a day-to-day basis. And when you do, you’ll have to get to know him all over again. And that’s the biggest drawback with online dating. Sometimes the person you fall for via text, email, or phone, is actually very different from the person you finally meet.

We don’t see a problem with moving forward, but honestly he seems like he’s still out there looking. So if you do decide to keep exploring this, please be careful.  You need to get to know him in person before you jump into something more serious, or actually visit him. In fact he should be the one visiting you if he’s truly serious about being in a relationship with you. And when he does, he should probably stay at a hotel or some other place of your choosing just to give you some space from him. (You could have him stay with a guy friend of yours, or a brother or something.)

But our gut tells us he is still surveying the landscape, and still on the lookout.

Best of luck to you,


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11 Comments on Online dating: Should I move forward?

  1. Dear Guys,
    I met a guy online.. I’ve never online dated before but I thought id try it. We talked for a few days and then he asked me to hang out. We went out to eat with a couple that is friends of mine and then just me and him went and had a drink and just talked. He stayed out with me until almost midnight even though he has to get up at 5 30 in the mornings during the week for work. The second time we went out he took me out with a group of his friends and then we left with one of his friends and his girlfriend to do our own thing. He took me home after and we ended up staying up til 7 in the morning just talking and hanging out. Tomorrow he is coming over after work to change a few light bulbs for me. I asked him if he could see us going anywhere. He said that he thinks I’m “cool as sh*t” and he could definitey see himself with me, but he isn’t over his ex cheating on him yet. He broke up with his ex 3 weeks ago, so I think that’s understandable. Id like to get to know him more anyway before I get in something serious. But id like to know from a guys point of view after reading his response about us going somewhere.. should I keep seeing him?

  2. @Melanie…..Why wouldn’t you keep seeing him? There is risk with being in a relationship or even dating. There’s nothing you can do about it. Trust your gut and proceed with caution. But you’re rushing this. It’s way too soon to inquire about a serious relationship. It makes you seem insecure and impatient. And even if you’re feeling these emotions/feelings don’t show them yet. Just relax and enjoy his company. Once it starts to get physical, or before, that’s a good time to start discussing these matters. And if he only broke up a few weeks ago he’s hardly ready for anything serious. Yes, you could be a rebound, but just go with the flow here and see how you feel as it moves forward. Come back and ask another question anytime.

  3. Dear guys,

    i am a 43yr old woman. i met a gentleman online. He did not have a picture and i dismissed his winks and e-mails. He waited for a week and sent me another e-mail so i replied saying that i wont chatt without a picture. So he sent his picture to me. i didnt care for his picture so i did not respond. After 5 days, i get an e-mail saying”i’m guessing that after seeing my picture you still have no interest. good luck” and signed his name. somehow this note got my attention. So i replied saying that i had a busy week i was going to reply.

    We started charting everyday.within 3 days he asked for us to meet up for dinner. he is ver clear that he is not looking for a friend but a relationship and would like to remarry. he has been divorced for 10yrs. He picked a high end restaurant.(i found out that he is a surgeon). I liked him more when we were together. i think the date went well. I text him after the date thanking him and letting him that i had a great time. his response”You are easy to talk to and you are very smart so i think our date went fine”. i asked him if he sees us on a second date and his response “yes”. The date was this past Monday. i knew that he had to go on a business trip on thursday coming back on Monday. i sent him tet Wednesday night” Hi… have a successful business trip. his reponse ” Thanks!!!!!”.

    I feel like since our date either he has not been communihcating or he answers in short. by the way we had dinner with wine, then he wanted us to get dessert and then he wanted us to stay for coffee. our date ended up being over 2hrs. Other thing that i found strange was he did not let myself pick wine for myself, he asked me if i liked red or white and i said red then he ordered red wine for me. lol not mad at that but was surprised. He is known at the restaurant that he took me to so may be he wanted me to try what he likes.

    do you guys think we will have a second date? i want it bad.

  4. @Bash…..Thanks for your donation. We do appreciate it. We wish we could give you a definitive answer or some sort of guarantee but we can’t. What we can say is that some men aren’t very good at communicating via phone, text, email, etc. Most men are much better at face-to-face interactions. But even beyond that, some men don’t even value regular communication and dismiss it as a “woman” thing. (We wish this wasn’t the case.) What these guys don’t realize is that lack of communication is often the demise of many relationships. So will he ask you out? We don’t see why not, but we don’t think you should contact him anymore to remind him. You’ve reached out enough. You sent him a text before his trip. That’s plenty. Now the ball is in his court. And based on his insistence on ordering your wine—something for which we don’t recommend to guys–he’s plenty confident enough to ask you on a second date. So our final take is: You need to be patient and let him do the reaching out. If he does, just be yourself and see how it goes. If he doesn’t in the next week or so, it’s likely he’s not interested? Questions? Feel free to ask away.

  5. Hi guys, he came back from the business trip and only heard from him this ast Thursday. He said he was down with the flu for a week. He said he wants us to go for date this Tuesday. All day Thursday he was texted me. Then he started to text Friday afternoon. Around 5pm Friday he asked what my plans for the evening were. I told him that i was going to dinner with friends. so he said he will order out and eat alone. Saturday morning at 7am got text asking me how my evening went. i told him that it went well and was in bed by 11pm. he told me how much of a good cook he is. so he said he would like to make me some dinner for 5pm. and he said only if im comfortable. i agreed but wondered why he always asks me with less time to get ready. i know he asked around 8am but wish he had asked me friday when he was texting all day. he text me the address. When i got there everything was perfect. It was the first time i see him on jeans and tshirt. Food was delicious. from soup, salad then main food some fancy pasta thing and he then made steak when i was there to go with the main course. Red wine Badeau.This was amazing. then it got darker, fire place lit. 10pm, i suggested that i would like to leave since i had 45minutes to drive back to the city but he insisted i stay. i made the move to kiss and then we were kssing all night He wanted some sex but i wasn’t comfortable yet. Oh.. from the trip he brought me a tshirt.While all seems perfect, on Sunday evening i went onto his profile he edited it and added more pictures. Things that he changed was the original profile said he was 48 not 49.1 child now is 2 kids. He had already told me about 2 kids from the first date and had already told me that he is not 48 but 53 on the first date. There are pictures of the kids and him in the house. He showed me around. Why did he edit the profile after i left his house? When i was leaving in the morning he kissed me and said see yu soon. Does this mean that he is still looking? When do people usually come out of this online thing? Is he really interested or was he bored? Remember i like him a lot but not desperate lol.

  6. oh. i forgot to ask.. i thanked him for dinner and tshirt at the end of this stay over. Am i supposed to send a thank you text for tshirt and dinner? I hope he doesn’t expect me to do all that for him. Perfect linen and fancy plates and fancy silverware. Just a little intimidated.

  7. @Bash……Sounds like the date went well. Try not to stress out about it. And just be yourself. We don’t think an extra thank you text is necessary, but it could also be an excuse to reach out to him and say hi, so it’s okay if you do. But let him keep taking the initiative. And keep us posted.

  8. Online dating confusion! // May 2, 2013 at 4:06 pm //

    Dear guys,

    I’m a 24 year old new to online dating. I found a guy who I thought would be interesting to get to know. I send him an interest along with access to my pictures on the site, and he accepted. When he accepted, my email address and phone number were automatically sent to him but his were not sent to me. However, his number is on his profile, and since I’m a paying member, I have access to it. It’s been a few weeks and he hasn’t emailed or gotten in touch with me via phone. Would it be strange if I texted him first? We are both in the medical field and therefore extremely busy…how do I know if he is just busy vs not interested? If i text him first will he think It’s strange? How do I proceed? Thank you!

  9. @Online dating confusion……..He’s got your info right? If so, we’d let him initiate. No guy is too busy for a woman they’re interested in. If you text him you won’t really know his level of interest. Be patient.

  10. online dating confusion // May 3, 2013 at 10:33 am //

    Hi Guys,

    Thanks for the input! I’m not 100% sure he has my info but I’m pretty sure he does. Either way, I think you’re right…be patient. I was leaning towards the same but just needed to have someone else say it. Thanks!

  11. @odc….You’re welcome.

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  1. Online Dating: I ended the date early because I freaked out; but I really like him | The Guy's Perspective
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